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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities

PF-04971729 PF04971729

Cas:1210344-57-2

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Assay 98%min ----------------------------------------------------------------------------------------------

High purity Various Specifications Ertugliflozin CAS:1210344-57-2

Cas:1210344-57-2

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Manufacturers

inquiry

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% PF-04971729 1210344-57-2 GMP Manufacturer

Cas:1210344-57-2

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new api, intermedi

Ertugliflozin

Cas:1210344-57-2

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

New production CAS 1210344-57-2 with best quality

Cas:1210344-57-2

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

β-L-Idopyranose, 1,6-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)- 1210344-57-2

Cas:1210344-57-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Qingdao Beluga Import and Export Co., LTD

PF-04971729 CAS:1210344-57-2 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediat

PF-04971729 CAS:1210344-57-2

Cas:1210344-57-2

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

β-L-Idopyranose, 1,6-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)-

Cas:1210344-57-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

PF-04971729

Cas:1210344-57-2

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Triumph International Development Limilted

Appearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By

Ertugliflozin

Cas:1210344-57-2

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Nanjing Fred Technology Co.,Ltd.

Ertugliflozin is one of the most competitive products in our company, we can supply it with good quality and best price. Appearance:White to off-white solid Storage:Room temperature, Keep in Dark Place. Package:According to the demand of customer App

Ertugliflozin

Cas:1210344-57-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

Ertugliflozin 1210344-57-2

Cas:1210344-57-2

Min.Order:100 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

β-L-Idopyranose, 1,6-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)-

Cas:1210344-57-2

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

Ertugliflozin/High quality/Best price

Cas:1210344-57-2

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Ertugliflozin

Cas:1210344-57-2

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

TaiChem Taizhou Limited

Established in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site

PF-04971729

Cas:1210344-57-2

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Siwei Development Group Ltd.

Product name: Ertugliflozin CAS No.:1210344-57-2 Molecule Formula:C22H25CIO7 Molecule Weight:436.88 Purity: 99.0% Package: 25kg/drum Description:White crystalline powder Manufacture Standards:Enterprise Standard TE

High Quality Ertugliflozin

Cas:1210344-57-2

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Hangzhou Huarong Pharm Co., Ltd.

1. DMF is available. Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has built platforms for the research, d

Ertugliflozin

Cas:1210344-57-2

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

PF-04971729

Cas:1210344-57-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages High purity, all above 98.5%, no impurities after dissolution We will test each batch to ensure quality OEM and private brand services designed for free Various cap colors available We can also provide MT1 peptide powd

PF-04971729 CAS1210344-57-2

Cas:1210344-57-2

Min.Order:1 Metric Ton

FOB Price: $35.0 / 65.0

Type:Trading Company

inquiry

Jiangsu Qianyu Molecular Technology Co., LTD.

Our Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an

Best OfferPF-04971729

Cas:1210344-57-2

Min.Order:0

Negotiable

Type:Trading Company

inquiry

EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

PF-04971729

Cas:1210344-57-2

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

API name: Ertugliflozin; Ertugliflozin etabonate CAS No.: 1210344-57-2 Chemical name: (1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol Formula: C22H25ClO7 Structure: Appearance:

Ertugliflozin; Ertugliflozin etabonate

Cas:1210344-57-2

Min.Order:1 Kilogram

FOB Price: $100.0

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W

PF-04971729

Cas:1210344-57-2

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

PF-04971729

Cas:1210344-57-2

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Golden Pharma Co., Limited

GOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation

PF-04971729

Cas:1210344-57-2

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

PF-04971729

Cas:1210344-57-2

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

inquiry

ACHIEVER SYSTEAM BIOCHEM CO., LTD.

We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to provide excellence in researching, manufacturing and drug discovery process. Our rese

Ertugliflozin PF-04971729

Cas:1210344-57-2

Min.Order:100 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Synthetic route

C28H35ClO8

C28H35ClO8

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With water; trifluoroacetic acid at 20℃; for 1h;92%
[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol; water at 30℃; for 8h;91.4%
[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]methanol

[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]methanol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol; water at 20℃; for 3h;89%
With palladium on activated charcoal; hydrogen In ethanol; ethyl acetate at 20℃; for 6h;80%
With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol; 1,2-dichloro-benzene at 25 - 30℃; under 1500.15 - 2625.26 Torr; for 6h;13.5 g
C50H59ClO8Si

C50H59ClO8Si

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With trifluoroacetic acid In water at 20℃; for 1h;85%
{(2S,3S)-3,4,5-tris-benzyloxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6,8-dioxa-bicyclo[3.2.1]oct-1-yl}-methanol
1210763-25-9

{(2S,3S)-3,4,5-tris-benzyloxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6,8-dioxa-bicyclo[3.2.1]oct-1-yl}-methanol

A

Ertugliflozin
1210344-57-2

Ertugliflozin

B

(1S,2S,3S,4S,5S)-5-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1-hydroxymethyl-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
1210344-58-3

(1S,2S,3S,4S,5S)-5-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1-hydroxymethyl-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

Conditions
ConditionsYield
With formic acid; palladium In tetrahydrofuran; ethanol at 20℃; for 2h;A 29%
B 15%
C28H37ClO7S2
1233482-00-2

C28H37ClO7S2

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With trifluoroacetic acid at 23℃; for 96h; stereoselective reaction;491 mg
(2R,3S,4S)-2,3,4-tris(benzyloxy)-1-(3-((benzyloxy)(4-ethoxyphenyl)methyl)-4-chlorophenyl)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-butan-1-one

(2R,3S,4S)-2,3,4-tris(benzyloxy)-1-(3-((benzyloxy)(4-ethoxyphenyl)methyl)-4-chlorophenyl)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-butan-1-one

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic acid; triethylsilane / toluene / 20 °C
2: 5%-palladium/activated carbon; hydrogenchloride; hydrogen / toluene; methanol; water / 18 h / 25 °C / 2585.81 Torr / Inert atmosphere
View Scheme
(2S,3S,4R)-2,3,4-tris(benzyloxy)-1-((benzyloxy)-methyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane
1629222-50-9

(2S,3S,4R)-2,3,4-tris(benzyloxy)-1-((benzyloxy)-methyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In methanol; water; toluene at 25℃; under 2585.81 Torr; for 18h; Inert atmosphere;
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In methanol; water; toluene at 25℃; under 2585.81 Torr; for 18h;
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
1298086-18-6

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 0.25h;
With sodium methylate In methanol at 20℃; for 3.25h; Inert atmosphere;
(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one oxalate
1431329-06-4

(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one oxalate

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate / toluene; water / 0.17 h / 20 °C
2.1: n-butyllithium / toluene; 2-methyltetrahydrofuran; hexane / -15 - 20 °C / Inert atmosphere
2.2: 0.17 h / -15 °C / Inert atmosphere
3.1: trifluoroacetic acid; triethylsilane / toluene / 20 °C
4.1: 5%-palladium/activated carbon; hydrogenchloride; hydrogen / toluene; methanol; water / 18 h / 25 °C / 2585.81 Torr / Inert atmosphere
View Scheme
(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one
1431329-05-3

(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / toluene; 2-methyltetrahydrofuran; hexane / -15 - 20 °C / Inert atmosphere
1.2: 0.17 h / -15 °C / Inert atmosphere
2.1: trifluoroacetic acid; triethylsilane / toluene / 20 °C
3.1: 5%-palladium/activated carbon; hydrogenchloride; hydrogen / toluene; methanol; water / 18 h / 25 °C / 2585.81 Torr / Inert atmosphere
View Scheme
(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: methanesulfonic acid / toluene; tetrahydrofuran; hexane / 25.83 h / -71 - 20 °C / Large scale
2.1: pyridinium p-toluenesulfonate / dichloromethane; water / 8 h / 20 °C / Large scale
3.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale
4.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale
4.2: 0.83 h / 55 °C / Large scale
5.1: SiliaBond tosic acid / dichloromethane / 18 h / 20 °C / Large scale
View Scheme
C34H59ClO7Si4
1528636-28-3

C34H59ClO7Si4

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane; water / 8 h / 20 °C / Large scale
2.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale
3.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale
3.2: 0.83 h / 55 °C / Large scale
4.1: SiliaBond tosic acid / dichloromethane / 18 h / 20 °C / Large scale
View Scheme
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1H-imidazole / dichloromethane / 1 h / 5 - 20 °C / Large scale
2.1: pyridinium p-toluenesulfonate / dichloromethane; water / 8 h / 20 °C / Large scale
3.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale
4.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale
4.2: 0.83 h / 55 °C / Large scale
5.1: SiliaBond tosic acid / dichloromethane / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 7 steps
1.1: triethylamine / dichloromethane / 10 - 30 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
2.2: 2 h / 0 - 30 °C
3.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
4.2: 2 h / -80 - 30 °C
5.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
6.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
7.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 8 steps
1.1: triethylamine / dichloromethane / 10 - 30 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
2.2: 2 h / 0 - 30 °C
3.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
4.2: 2 h / -80 - 30 °C
5.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
6.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
7.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
8.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
((2R,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris(trimethylsilyloxy)tetrahydro-2H-pyran-2-yl)methanol
1528636-29-4

((2R,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris(trimethylsilyloxy)tetrahydro-2H-pyran-2-yl)methanol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale
2.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale
2.2: 0.83 h / 55 °C / Large scale
3.1: SiliaBond tosic acid / dichloromethane / 18 h / 20 °C / Large scale
View Scheme
(2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1528636-39-6

(2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With SiliaBond tosic acid In dichloromethane at 20℃; for 18h; Large scale;
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-hexyllithium / toluene; tetrahydrofuran; hexane / 1 h / -84 - -74 °C / Large scale
1.2: 2 h / -74 - -15 °C / Large scale
2.1: methanesulfonic acid / toluene; tetrahydrofuran; hexane / 25.83 h / -71 - 20 °C / Large scale
3.1: pyridinium p-toluenesulfonate / dichloromethane; water / 8 h / 20 °C / Large scale
4.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale
5.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale
5.2: 0.83 h / 55 °C / Large scale
6.1: SiliaBond tosic acid / dichloromethane / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - -65 °C
1.2: 6 h / -25 - 20 °C
2.1: 1H-imidazole / dichloromethane / 0 - 35 °C
3.1: toluene-4-sulfonic acid; pyridine / water / 0 - 35 °C
4.1: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 0 - 10 °C
5.1: sodium ethanolate / ethanol / 50 - 55 °C
6.1: methanesulfonic acid / dichloromethane / 5 h / 25 - 35 °C
View Scheme
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-hexyllithium / toluene; tetrahydrofuran; hexane / 1 h / -84 - -74 °C / Large scale
1.2: 2 h / -74 - -15 °C / Large scale
2.1: methanesulfonic acid / toluene; tetrahydrofuran; hexane / 25.83 h / -71 - 20 °C / Large scale
3.1: pyridinium p-toluenesulfonate / dichloromethane; water / 8 h / 20 °C / Large scale
4.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale
5.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale
5.2: 0.83 h / 55 °C / Large scale
6.1: SiliaBond tosic acid / dichloromethane / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 8 steps
1.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
1.2: 3 h / -75 - -60 °C
1.3: 18 h / -75 - 25 °C
2.1: triethylamine / dichloromethane / 10 - 30 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
3.2: 2 h / 0 - 30 °C
4.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
5.2: 2 h / -80 - 30 °C
6.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
7.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
8.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
1.2: 3 h / -75 - -60 °C
1.3: 18 h / -75 - 25 °C
2.1: triethylamine / dichloromethane / 10 - 30 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
3.2: 2 h / 0 - 30 °C
4.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
5.2: 2 h / -80 - 30 °C
6.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
7.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
9.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one

3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
1.2: 3 h / -75 - -60 °C
1.3: 18 h / -75 - 25 °C
2.1: triethylamine / dichloromethane / 10 - 30 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
3.2: 2 h / 0 - 30 °C
4.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
5.2: 2 h / -80 - 30 °C
6.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
7.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
8.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
1.2: 3 h / -75 - -60 °C
1.3: 18 h / -75 - 25 °C
2.1: triethylamine / dichloromethane / 10 - 30 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
3.2: 2 h / 0 - 30 °C
4.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
5.2: 2 h / -80 - 30 °C
6.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
7.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
9.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
5-bromo-2-chlorobenzoic acid
21739-92-4

5-bromo-2-chlorobenzoic acid

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C
1.2: 2 h / 0 - 10 °C
2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
3.2: 3 h / -75 - -60 °C
3.3: 18 h / -75 - 25 °C
4.1: triethylamine / dichloromethane / 10 - 30 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
5.2: 2 h / 0 - 30 °C
6.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
7.2: 2 h / -80 - 30 °C
8.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
9.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
10.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 11 steps
1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C
1.2: 2 h / 0 - 10 °C
2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
3.2: 3 h / -75 - -60 °C
3.3: 18 h / -75 - 25 °C
4.1: triethylamine / dichloromethane / 10 - 30 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
5.2: 2 h / 0 - 30 °C
6.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
7.2: 2 h / -80 - 30 °C
8.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
9.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
10.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
11.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 6 steps
1.1: N,N-dimethyl-formamide / N,N-dimethyl-formamide / 12 h / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C
3.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C
4.2: 48 h / -78 - 20 °C
5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
6.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: N,N-dimethyl-formamide / N,N-dimethyl-formamide / 12 h / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C
3.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
4.1: magnesium; methyl iodide / tetrahydrofuran / 1 h / Reflux
4.2: 3 h / -20 - 20 °C
5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.25 h / -78 °C
5.2: 13.25 h / -78 - 20 °C
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
7.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: N,N-dimethyl-formamide / N,N-dimethyl-formamide / 12 h / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C
3.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C
4.2: 3 h / -78 °C
5.1: acetonitrile / 12 h / Reflux
5.2: 3 h / 20 °C
6.1: toluene / 12 h / Reflux
7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
8.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
Phenetole
103-73-1

Phenetole

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C
1.2: 2 h / 0 - 10 °C
2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
3.2: 3 h / -75 - -60 °C
3.3: 18 h / -75 - 25 °C
4.1: triethylamine / dichloromethane / 10 - 30 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
5.2: 2 h / 0 - 30 °C
6.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
7.2: 2 h / -80 - 30 °C
8.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
9.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
10.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 11 steps
1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C
1.2: 2 h / 0 - 10 °C
2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
3.2: 3 h / -75 - -60 °C
3.3: 18 h / -75 - 25 °C
4.1: triethylamine / dichloromethane / 10 - 30 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
5.2: 2 h / 0 - 30 °C
6.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
7.2: 2 h / -80 - 30 °C
8.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
9.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
10.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
11.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 5 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C
3.2: 48 h / -78 - 20 °C
4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
5.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
3.1: magnesium; methyl iodide / tetrahydrofuran / 1 h / Reflux
3.2: 3 h / -20 - 20 °C
4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.25 h / -78 °C
4.2: 13.25 h / -78 - 20 °C
5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
6.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C
3.2: 3 h / -78 °C
4.1: acetonitrile / 12 h / Reflux
4.2: 3 h / 20 °C
5.1: toluene / 12 h / Reflux
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
7.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
461432-22-4

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
2.2: 3 h / -75 - -60 °C
2.3: 18 h / -75 - 25 °C
3.1: triethylamine / dichloromethane / 10 - 30 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
4.2: 2 h / 0 - 30 °C
5.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
6.2: 2 h / -80 - 30 °C
7.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
8.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
10.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 9 steps
1.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
2.2: 3 h / -75 - -60 °C
2.3: 18 h / -75 - 25 °C
3.1: triethylamine / dichloromethane / 10 - 30 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
4.2: 2 h / 0 - 30 °C
5.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
6.2: 2 h / -80 - 30 °C
7.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
8.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
9.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C
2.2: 48 h / -78 - 20 °C
3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
4.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
2.1: magnesium; methyl iodide / tetrahydrofuran / 1 h / Reflux
2.2: 3 h / -20 - 20 °C
3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.25 h / -78 °C
3.2: 13.25 h / -78 - 20 °C
4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
5.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C
2.2: 3 h / -78 °C
3.1: acetonitrile / 12 h / Reflux
3.2: 3 h / 20 °C
4.1: toluene / 12 h / Reflux
5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid / water; acetone / 12 h / 20 °C
6.1: trifluoroacetic acid / water / 1 h / 20 °C
View Scheme
(2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

(2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
1.2: 2 h / 0 - 30 °C
2.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
3.2: 2 h / -80 - 30 °C
4.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
5.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
6.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
1.2: 2 h / 0 - 30 °C
2.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
3.2: 2 h / -80 - 30 °C
4.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
5.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
6.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
7.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxyl]silane

tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxyl]silane

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
2.2: 2 h / -80 - 30 °C
3.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
4.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
5.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 6 steps
1.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
2.2: 2 h / -80 - 30 °C
3.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
4.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
6.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol

[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
1.2: 2 h / -80 - 30 °C
2.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
3.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 5 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
1.2: 2 h / -80 - 30 °C
2.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
3.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
4.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
5.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 15 h / 0 - 40 °C
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
2.2: 3 h / -75 - -60 °C
2.3: 18 h / -75 - 25 °C
3.1: triethylamine / dichloromethane / 10 - 30 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
4.2: 2 h / 0 - 30 °C
5.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
6.2: 2 h / -80 - 30 °C
7.1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
8.1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
10.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 9 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 15 h / 0 - 40 °C
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
2.2: 3 h / -75 - -60 °C
2.3: 18 h / -75 - 25 °C
3.1: triethylamine / dichloromethane / 10 - 30 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C
4.2: 2 h / 0 - 30 °C
5.1: acetyl chloride; methanol / dichloromethane / 0.5 h / 25 - 30 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -80 - -65 °C
6.2: 2 h / -80 - 30 °C
7.1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
8.1: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
9.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide / N,N-dimethyl-formamide; water / 5 h / 10 - 30 °C
2: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
3: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
Multi-step reaction with 4 steps
1: potassium hydroxide / N,N-dimethyl-formamide; water / 8 h / 10 - 30 °C
2: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
3: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
4: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
methyl 2,3,4-tri-O-benzyl-1-C-[4-chloro-3-(4-ethoxybenzyl)phenyl]-5-(hydroxymethyl)-α-D-gluco-hexodialdo-1,5-pyranoside

methyl 2,3,4-tri-O-benzyl-1-C-[4-chloro-3-(4-ethoxybenzyl)phenyl]-5-(hydroxymethyl)-α-D-gluco-hexodialdo-1,5-pyranoside

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; methanol / 1 h / 20 - 25 °C
2: trifluoroacetic acid / dichloromethane / 5 h / -10 - 30 °C
3: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol; 1,2-dichloro-benzene / 6 h / 25 - 30 °C / 1500.15 - 2625.26 Torr
View Scheme
(2R,3S,4S)-2,3,4-tribenzyloxy-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxanepent-4-yl)-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)butan-1-one

(2R,3S,4S)-2,3,4-tribenzyloxy-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxanepent-4-yl)-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)butan-1-one

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 40 - 50℃; under 1500.15 Torr;
C42H57ClO11

C42H57ClO11

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 30 - 35℃;
Ertugliflozin
1210344-57-2

Ertugliflozin

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(4aS,7S,8R,9R,9aS)-7-(4-chloro-3-(4-ethoxybenzyl)phenyl)-2-phenylhexahydro-4a,7-epoxy[1,3]dioxino[5,4-c]oxepine-8,9-diol

(4aS,7S,8R,9R,9aS)-7-(4-chloro-3-(4-ethoxybenzyl)phenyl)-2-phenylhexahydro-4a,7-epoxy[1,3]dioxino[5,4-c]oxepine-8,9-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile at 20 - 30℃; for 0.5h; Inert atmosphere;100%
Ertugliflozin
1210344-57-2

Ertugliflozin

acetic anhydride
108-24-7

acetic anhydride

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
1298086-18-6

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Conditions
ConditionsYield
With pyridine In toluene at 5 - 20℃; for 24.25h; Inert atmosphere;89%
With pyridine In toluene at 5 - 20℃; for 24.25h;5.4%
Ertugliflozin
1210344-57-2

Ertugliflozin

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

(1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid
1210344-83-4

(1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: Ertugliflozin In methanol; water; isopropyl alcohol at 40 - 60℃; under 30 Torr;
Stage #2: L-Pyroglutamic acid In methanol; water; isopropyl alcohol at 40 - 80℃;
85.3%
In water; isopropyl alcohol at 40 - 80℃; for 10h; Inert atmosphere;85%
In ethanol; water at 75 - 80℃;78%
In water at 25 - 30℃; for 2.5h; Solvent;0.472 g
In acetonitrile at 25 - 30℃; for 0.25h;1.1 g
Ertugliflozin
1210344-57-2

Ertugliflozin

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,4aS,7S,8R,9R,9aS)-7-[4-chloro-3-(4-ethoxybenzyl)phenyl]-2-phenyltetrahydro-4a,7-epoxy[1,3]dioxino[5,4-c]oxepine-8,9(4H,5H)-diol

(2R,4aS,7S,8R,9R,9aS)-7-[4-chloro-3-(4-ethoxybenzyl)phenyl]-2-phenyltetrahydro-4a,7-epoxy[1,3]dioxino[5,4-c]oxepine-8,9(4H,5H)-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 16h;84%
Ertugliflozin
1210344-57-2

Ertugliflozin

acetic anhydride
108-24-7

acetic anhydride

[(1R,2S,3S,4R,5S)-2,3,4-triacetoxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]acetic acid methyl ester

[(1R,2S,3S,4R,5S)-2,3,4-triacetoxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]acetic acid methyl ester

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 3h;82%
Ertugliflozin
1210344-57-2

Ertugliflozin

acetic anhydride
108-24-7

acetic anhydride

((1R,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)-phenyl)-2,3,4-trihydroxy-6,8-dioxabicyclo[3.2.1]octan-1-yl)methyl acetate
1298086-20-0

((1R,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)-phenyl)-2,3,4-trihydroxy-6,8-dioxabicyclo[3.2.1]octan-1-yl)methyl acetate

Conditions
ConditionsYield
With pyridine In toluene at -10 - 20℃; for 8.28333h;79.7%
With pyridine In toluene at -10 - 20℃; for 19.1h; Inert atmosphere;19.2 g
Ertugliflozin
1210344-57-2

Ertugliflozin

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

C50H37ClN4O19
1292821-53-4

C50H37ClN4O19

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 60℃;73%
Ertugliflozin
1210344-57-2

Ertugliflozin

methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2S,3S,4R,5S)-4-(acetyloxy)-5-[4-chloro-3-(4-ethoxybenzyl)phenyl]-2-hydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-yl]oxy}tetrahydro-2H-pyran-2-carboxylate

methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2S,3S,4R,5S)-4-(acetyloxy)-5-[4-chloro-3-(4-ethoxybenzyl)phenyl]-2-hydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-yl]oxy}tetrahydro-2H-pyran-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 16 h / 80 °C
2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 - -10 °C / Molecular sieve
2.2: 72 h / 23 °C
3.1: trifluoroacetic acid / dichloromethane; water / 19 h / 23 °C
View Scheme
Ertugliflozin
1210344-57-2

Ertugliflozin

C28H32ClO13(1-)*Na(1+)

C28H32ClO13(1-)*Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 16 h / 80 °C
2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 - -10 °C / Molecular sieve
2.2: 72 h / 23 °C
3.1: trifluoroacetic acid / dichloromethane; water / 19 h / 23 °C
4.1: sodium hydroxide / water; methanol / 16 h / 23 °C
View Scheme
Ertugliflozin
1210344-57-2

Ertugliflozin

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,4aS,7S,8R,9S,9aS)-8-(acetyloxy)-7-[4-chloro-3-(4-ethoxybenzyl)phenyl]-2-phenyltetrahydro-4a,7-epoxy[1,3]dioxino[5,4-c]oxepin-9(4H,5H)-yl methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosiduronate

(2R,4aS,7S,8R,9S,9aS)-8-(acetyloxy)-7-[4-chloro-3-(4-ethoxybenzyl)phenyl]-2-phenyltetrahydro-4a,7-epoxy[1,3]dioxino[5,4-c]oxepin-9(4H,5H)-yl methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosiduronate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 16 h / 80 °C
2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 - -10 °C / Molecular sieve
2.2: 72 h / 23 °C
View Scheme
Ertugliflozin
1210344-57-2

Ertugliflozin

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

(1R,2S,3S,4R,5R)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol L-pyroglutamic acid

(1R,2S,3S,4R,5R)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol L-pyroglutamic acid

Conditions
ConditionsYield
With water In isopropyl alcohol at 20 - 55℃; for 3h; Large scale;9.59 kg
Ertugliflozin
1210344-57-2

Ertugliflozin

(1S,2S,3S,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-ol

(1S,2S,3S,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / acetonitrile / 0.5 h / 20 - 30 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 30 °C / Inert atmosphere
2.2: 12 h / 0 - 30 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / acetonitrile / 12 h / 20 - 30 °C / Inert atmosphere
View Scheme

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