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
Cas:1210344-57-2
Min.Order:1 Kilogram
FOB Price: $3.0
Type:Lab/Research institutions
inquiryItems Standard Result Assay 98%min ----------------------------------------------------------------------------------------------
Cas:1210344-57-2
Min.Order:1 Gram
FOB Price: $100.0 / 500.0
Type:Manufacturers
inquiry1. 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
Cas:1210344-57-2
Min.Order:1 Gram
FOB Price: $0.1
Type:Manufacturers
inquiryCangzhou 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
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
Cas:1210344-57-2
Min.Order:1 Kilogram
FOB Price: $139.0 / 210.0
Type:Trading Company
inquiry1.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
Cas:1210344-57-2
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryPF-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
Cas:1210344-57-2
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryHello, 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
Cas:1210344-57-2
Min.Order:1 Kilogram
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inquiryAdvantage : 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&
Cas:1210344-57-2
Min.Order:0
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Type:Lab/Research institutions
inquiryOur 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
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
Cas:1210344-57-2
Min.Order:0 Metric Ton
Negotiable
Type:Lab/Research institutions
inquiryErtugliflozin 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
Cas:1210344-57-2
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryOur 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-
Cas:1210344-57-2
Min.Order:100 Milligram
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Type:Lab/Research institutions
inquiryCompany 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
Cas:1210344-57-2
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryJ&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
Cas:1210344-57-2
Min.Order:0
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Type:Lab/Research institutions
inquiryMassive 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
Cas:1210344-57-2
Min.Order:1 Gram
FOB Price: $1.0
Type:Lab/Research institutions
inquiryZibo 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
Cas:1210344-57-2
Min.Order:10 Gram
FOB Price: $100.0
Type:Lab/Research institutions
inquiryEstablished 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
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
Cas:1210344-57-2
Min.Order:1 Kilogram
Negotiable
Type:Trading Company
inquiry1. 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
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,
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
Cas:1210344-57-2
Min.Order:1 Metric Ton
FOB Price: $35.0 / 65.0
Type:Trading Company
inquiryOur 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
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
Cas:1210344-57-2
Min.Order:1 Kilogram
FOB Price: $18.0 / 20.0
Type:Trading Company
inquiryAPI 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:
Cas:1210344-57-2
Min.Order:1 Kilogram
FOB Price: $100.0
Type:Trading Company
inquiryShandong 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
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
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
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
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
Cas:1210344-57-2
Min.Order:100 Gram
FOB Price: $1.0
Type:Lab/Research institutions
inquiryErtugliflozin
Conditions | Yield |
---|---|
With water; trifluoroacetic acid at 20℃; for 1h; | 92% |
Ertugliflozin
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol; water at 30℃; for 8h; | 91.4% |
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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
A
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
Conditions | Yield |
---|---|
With formic acid; palladium In tetrahydrofuran; ethanol at 20℃; for 2h; | A 29% B 15% |
C28H37ClO7S2
Ertugliflozin
Conditions | Yield |
---|---|
With trifluoroacetic acid at 23℃; for 96h; stereoselective reaction; | 491 mg |
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
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 |
Ertugliflozin
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 40 - 50℃; under 1500.15 Torr; |
Ertugliflozin
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 30 - 35℃; |
Ertugliflozin
benzaldehyde dimethyl acetal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetonitrile at 20 - 30℃; for 0.5h; Inert atmosphere; | 100% |
Ertugliflozin
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
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
benzaldehyde dimethyl acetal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 16h; | 84% |
Ertugliflozin
acetic anhydride
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at 20℃; for 3h; | 82% |
Ertugliflozin
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
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 60℃; | 73% |
Ertugliflozin
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
benzaldehyde dimethyl acetal
Conditions | Yield |
---|---|
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
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With water In isopropyl alcohol at 20 - 55℃; for 3h; Large scale; | 9.59 kg |
Ertugliflozin
Conditions | Yield |
---|---|
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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