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Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe

Atazanavir Manufacturer/High quality/Best price/In stock

Cas:198904-31-3

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality Atazanavir supplier in China

Cas:198904-31-3

Min.Order:1 Kilogram

Negotiable

Type:Manufacturers

inquiry

Wuhan Fortuna Chemical Co.,Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; ...... Appearance:White to almost white crystalline powder Storage:-20°C Freeze

Good quality Atazanavir powder CAS 198904-31-3 for antiviral use

Cas:198904-31-3

Min.Order:100 Gram

FOB Price: $1.2 / 2.9

Type:Trading Company

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Jinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pu

Atazanavir 198904-31-3 manufacturer/supplier

Cas:198904-31-3

Min.Order:1 Gram

Negotiable

Type:Manufacturers

inquiry

Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

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% Atazanavir 198904-31-3 GMP Manufacturer

Cas:198904-31-3

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Atazanavir

Cas:198904-31-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

TIANFU CHEM---Atazanavir

Cas:198904-31-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

Atazanavir CAS 198904-31-3

Cas:198904-31-3

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

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

Pharmaceutical Grade CAS 198904-31-3 with competitive price

Cas:198904-31-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

Name:Atazanavir CAS: 198904-31-3 Molecular Formula:C38H52N6O7 Property: white powder Assay: 99% A

Atazanavir CAS: 198904-31-3

Cas:198904-31-3

Min.Order:5 Metric Ton

FOB Price: $1.0 / 2.0

Type:Other

inquiry

Henan Wentao Chemical Product Co., Ltd.

We are leading fine chemicals supplier in China with ISO certificate, Our main business covers the fields below: 1.Noble Metal Catalysts (Pt.Pd...) 2.Organic Phosphine Ligands (Tert-butyl-phosphine.Cyclohexyl-phosphine...) 3.OLED

Hubei Langyou International Trading Co., Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta

high quality 198904-31-3 Atazanavir with best price

Cas:198904-31-3

Min.Order:10 Gram

Negotiable

Type:Other

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

Qingdao Beluga Import and Export Co., LTD

Atazanavir CAS:198904-31-3 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 intermediates

Atazanavir CAS:198904-31-3

Cas:198904-31-3

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

Atazanavir

Cas:198904-31-3

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 Wonda Pharm Limited

1.high quality: quality is life. quality is the most important element for all goods. we have a lab doing research in wuhan china. hplc and nmr is available if needed. 2.reasonable price: we provide high quality products with competi

high purity 99% Atazanavir CAS 198904-31-3 with lower price

Cas:198904-31-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Mojin Biotechnology Co.,Ltd

Hebei Mojin Biotechnology Co., Ltd, Our company is a professional chemical raw materials and chemical reagents research and development production enterprises. We have several production line,So we can control the lowest price. We also have several

Atazanavir cas:198904-31-3

Cas:198904-31-3

Min.Order:25 Gram

FOB Price: $90.0 / 100.0

Type:Trading Company

inquiry

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

Atazanavir

Cas:198904-31-3

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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-

Atazanavir 198904-31-3

Cas:198904-31-3

Min.Order:200 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

Atazanavir

Cas:198904-31-3

Min.Order:0 Metric Ton

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

Atazanavir

Cas:198904-31-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

3-FLUORO-L-PHENYLALANINE

Cas:198904-31-3

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Fonlynn Health Technology Co., Ltd.

Packing: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Transportation:Express/Sea/Air Port:Ningbo/Shanghai/Qingd

Atazanavir

Cas:198904-31-3

Min.Order:0

Negotiable

Type:Trading Company

inquiry

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

Henan Kanbei Chemical Co.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

Atazanavir

Cas:198904-31-3

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

Atazanavir/High quality/Best price

Cas:198904-31-3

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

Antibiotics Atazanavir Powder

Cas:198904-31-3

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov

Atazanavir

Cas:198904-31-3

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

Synthetic route

C14H18N4O4
869285-68-7

C14H18N4O4

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With dipotassium hydrogenphosphate In water at 5 - 40℃;100%
{(S)-1-[N'-((2S,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester
857900-54-0

{(S)-1-[N'-((2S,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane95%
C14H18N4O4
869285-68-7

C14H18N4O4

1-[4-(Pyridin-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane.3hydrochloride

1-[4-(Pyridin-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane.3hydrochloride

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With dipotassium hydrogenphosphate In water at 5 - 40℃; for 1.5 - 2h;95%
1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-(5S)-2,5-diamino-6-phenyl-2-azahexane

1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-(5S)-2,5-diamino-6-phenyl-2-azahexane

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 35℃; for 1.5h; Temperature; Concentration;91.6%
(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester
857904-02-0

(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester

methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate
1192510-20-5

methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
In dichloromethane for 64h; Silica gel;87%
silica gel In dichloromethane for 64h;87%
In isopropyl alcohol at 90℃; for 12h;
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With 4-methyl-morpholine; diisopropyl-carbodiimide In dichloromethane; isopropyl alcohol at -10 - 20℃; Product distribution / selectivity; Inert atmosphere;84%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 22 - 25℃; Reagent/catalyst; Large scale;82.1%
With O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight; Yield given. Multistep reaction;
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane
437713-06-9

1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With thionyl chloride; triethylamine In dichloromethane at 42℃; for 3h;
Stage #2: 1-[4-(pyridine-2-yl)phenyl]-(5S)-2,5-diamino-(4S)-hydroxy-6-phenyl-2-azahexane In dichloromethane at 20℃; Solvent; Temperature; Concentration;
74.2%
1-[4-(pyridin-2-yl)phenyl]-5(S)-2,5-bis{[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4-oxo-6-phenyl-2-azahexane

1-[4-(pyridin-2-yl)phenyl]-5(S)-2,5-bis{[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4-oxo-6-phenyl-2-azahexane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With sodium tetrahydroborate In 2-methyltetrahydrofuran for 4h; Cooling with ice;70%
With lithium tri-t-butoxyaluminum hydride In diethyl ether at 0℃; for 4h; diastereoselective reaction;39 g
1-(4-(pyridin-2-yl)benzyl)hydrazine
920757-34-2

1-(4-(pyridin-2-yl)benzyl)hydrazine

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 14.43 g / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 / 1.5 h / 20 °C
2: 25 percent / propan-2-ol / 24 h / Heating
3: HCl / tetrahydrofuran; H2O / 5 h / 50 °C
4: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2
View Scheme
(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester
857904-02-0

(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 25 percent / propan-2-ol / 24 h / Heating
2: HCl / tetrahydrofuran; H2O / 5 h / 50 °C
3: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1.1: sodium iodide / acetonitrile / 0.25 h / 20 °C
1.2: 0.25 h / 20 °C
2.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C
View Scheme
{(1S,2S)-1-benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propyl}-carbamic acid tert-butyl ester
857904-03-1

{(1S,2S)-1-benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propyl}-carbamic acid tert-butyl ester

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / tetrahydrofuran; H2O / 5 h / 50 °C
2: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2
View Scheme
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 25 percent / propan-2-ol / 24 h / Heating
2: HCl / tetrahydrofuran; H2O / 5 h / 50 °C
3: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale
2: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale
3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale
View Scheme
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 14.43 g / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 / 1.5 h / 20 °C
2: 25 percent / propan-2-ol / 24 h / Heating
3: HCl / tetrahydrofuran; H2O / 5 h / 50 °C
4: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -25 - 20 °C
2.1: sodium iodide / acetonitrile / 0.25 h / 20 °C
2.2: 0.25 h / 20 °C
3.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / ethyl acetate / 0.5 h
1.2: 16 h
2.1: hydrogenchloride / tetrahydrofuran / 2 h / 20 °C
3.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere
3.2: 4 h / Inert atmosphere; Reflux
4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr
5.1: sodium iodide / acetonitrile / 0.25 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 - 25 °C
2: dipotassium hydrogenphosphate / water / 5 - 40 °C
View Scheme
N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine
198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: HCl / tetrahydrofuran; H2O / 3 h / 50 °C
2: 14.43 g / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 / 1.5 h / 20 °C
3: 25 percent / propan-2-ol / 24 h / Heating
4: HCl / tetrahydrofuran; H2O / 5 h / 50 °C
5: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1: 69 percent / propan-2-ol / 16 h / Heating
2: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C
3: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight
View Scheme
Multi-step reaction with 3 steps
1: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale
2: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale
3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale
View Scheme
2-bromo-pyridine
109-04-6

2-bromo-pyridine

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Mg, I2, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl
2: 93 percent / ethanol / 4 h / Heating
3: 89 percent / H2 / 10percent Pd/C / methanol
4: 69 percent / propan-2-ol / 16 h / Heating
5: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C
6: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight
View Scheme
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 20 h / 76 °C / Inert atmosphere
2: toluene; isopropyl alcohol / 2 h / 80 - 85 °C / Inert atmosphere; Large scale
3: palladium 10% on activated carbon; sodium formate / water; ethanol / 1.5 h / 57 °C
4: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale
5: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale
6: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale
View Scheme
2-(4-formylphenyl)pyridine
127406-56-8

2-(4-formylphenyl)pyridine

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 93 percent / ethanol / 4 h / Heating
2: 89 percent / H2 / 10percent Pd/C / methanol
3: 69 percent / propan-2-ol / 16 h / Heating
4: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C
5: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight
View Scheme
Multi-step reaction with 5 steps
1: toluene; isopropyl alcohol / 2 h / 80 - 85 °C / Inert atmosphere; Large scale
2: palladium 10% on activated carbon; sodium formate / water; ethanol / 1.5 h / 57 °C
3: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale
4: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale
5: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere
1.2: 4 h / Inert atmosphere; Reflux
2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr
3.1: sodium iodide / acetonitrile / 0.25 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C
View Scheme
L-tert-Leucine
20859-02-3

L-tert-Leucine

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / 2N aq. NaOH / dioxane / 18 h / 60 °C
2: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water / 18 h / 60 °C
1.2: 25 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 25 - 30 °C
2.2: 3 h
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / tetrahydrofuran / 60 °C
2.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -25 - 20 °C
3.1: sodium iodide / acetonitrile / 0.25 h / 20 °C
3.2: 0.25 h / 20 °C
4.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydroxide / tetrahydrofuran / 60 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / ethyl acetate / 0.5 h
2.2: 16 h
3.1: hydrogenchloride / tetrahydrofuran / 2 h / 20 °C
4.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere
4.2: 4 h / Inert atmosphere; Reflux
5.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr
6.1: sodium iodide / acetonitrile / 0.25 h / 20 °C
6.2: 0.25 h / 20 °C
7.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C
View Scheme
1,1-dimethoxy-1-(4-bromophenyl)methane
24856-58-4

1,1-dimethoxy-1-(4-bromophenyl)methane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Mg, I2, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl
2: 93 percent / ethanol / 4 h / Heating
3: 89 percent / H2 / 10percent Pd/C / methanol
4: 69 percent / propan-2-ol / 16 h / Heating
5: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C
6: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight
View Scheme
Multi-step reaction with 6 steps
1.1: magnesium; iodine / tetrahydrofuran / 2 h / 20 °C / Heating
1.2: 2.25 h / 20 °C
2.1: hydrogenchloride / water; tetrahydrofuran / Cooling with ice
3.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere
3.2: 4 h / Inert atmosphere; Reflux
4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr
5.1: sodium iodide / acetonitrile / 0.25 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C
View Scheme
N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine
857904-11-1

N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / H2 / 10percent Pd/C / methanol
2: 69 percent / propan-2-ol / 16 h / Heating
3: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C
4: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight
View Scheme
1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane
198904-86-8

1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C
2: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale
2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / dichloromethane; water / 0.5 - 40 °C
2: dipotassium hydrogenphosphate / water / 5 - 40 °C
View Scheme
N-methoxycarbonyl-(L)-tert-leucine

N-methoxycarbonyl-(L)-tert-leucine

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
In ethanol; dichloromethane; water; ethyl acetate
In ethanol; dichloromethane; water; ethyl acetate
C36H50N6O5
1028634-76-5

C36H50N6O5

methyl chloroformate
79-22-1

methyl chloroformate

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 2.5h;
(2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol hydrochloride

(2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol hydrochloride

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25 - 30℃;
Stage #2: (2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane; water for 3h; Product distribution / selectivity;
methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate
1192510-20-5

methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water / 60 - 65 °C
2.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C
3.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere
3.2: 16 h / 10 - 35 °C
View Scheme
Multi-step reaction with 3 steps
1.1: water; dichloromethane / 40 - 65 °C
2.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C
3.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere
3.2: 10 - 15 °C
3.3: 10 - 35 °C
View Scheme
1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane
198905-04-3

1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C
2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere
2.2: 16 h / 10 - 35 °C
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C
2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere
2.2: 10 - 15 °C
2.3: 10 - 35 °C
View Scheme
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride

1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With thionyl chloride; benzotriazol-1-ol; triethylamine In dichloromethane at -5 - 15℃; for 3.5h; Inert atmosphere;
Stage #2: 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride With dipotassium hydrogenphosphate In dichloromethane; water at 10 - 35℃; for 16h;
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With thionyl chloride; benzotriazol-1-ol; triethylamine In dichloromethane at -5 - 20℃; Inert atmosphere;
Stage #2: With dipotassium hydrogenphosphate In dichloromethane; water at 10 - 15℃;
Stage #3: 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride In dichloromethane; water at 10 - 35℃;
(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane
162536-40-5

(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride; water / tetrahydrofuran / 4 h / 50 - 55 °C
2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
2.2: 12 h / 30 - 35 °C
3.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; water / 3 h / 0 - 10 °C
4.1: water / 60 - 65 °C
5.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C
6.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere
6.2: 16 h / 10 - 35 °C
View Scheme
Multi-step reaction with 6 steps
1.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 50 - 55 °C
2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
2.2: 10 - 15 °C
2.3: 12 h / 30 - 35 °C
3.1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 3 h / 0 - 10 °C
4.1: water; dichloromethane / 40 - 65 °C
5.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C
6.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere
6.2: 10 - 15 °C
6.3: 10 - 35 °C
View Scheme
(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride
369362-96-9

(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
1.2: 12 h / 30 - 35 °C
2.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; water / 3 h / 0 - 10 °C
3.1: water / 60 - 65 °C
4.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C
5.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere
5.2: 16 h / 10 - 35 °C
View Scheme
Multi-step reaction with 5 steps
1.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
1.2: 10 - 15 °C
1.3: 12 h / 30 - 35 °C
2.1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 3 h / 0 - 10 °C
3.1: water; dichloromethane / 40 - 65 °C
4.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C
5.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere
5.2: 10 - 15 °C
5.3: 10 - 35 °C
View Scheme
methyl [(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate

methyl [(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; water / 3 h / 0 - 10 °C
2.1: water / 60 - 65 °C
3.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C
4.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere
4.2: 16 h / 10 - 35 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 3 h / 0 - 10 °C
2.1: water; dichloromethane / 40 - 65 °C
3.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C
4.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere
4.2: 10 - 15 °C
4.3: 10 - 35 °C
View Scheme
atazanavir
198904-31-3

atazanavir

atazanavir sulphate

atazanavir sulphate

Conditions
ConditionsYield
With sulfuric acid In acetone at 0 - 50℃; for 2h;95%
With sulfuric acid In ethanol at 20 - 30℃; Temperature; Concentration;95.2%
With sulfuric acid; pyrographite In 1,2-dimethoxyethane; dimethyl sulfoxide at 35℃; Solvent; Inert atmosphere;94%
atazanavir
198904-31-3

atazanavir

1-[4-(pyridin-2-yl)phenyl]-(S)-2,5-bis{[N-(methoxycarbonyl)-L-tert-leucyl]amino}-4-(S)-hydroxy-6-phenyl-2-azahexane hydrobromide

1-[4-(pyridin-2-yl)phenyl]-(S)-2,5-bis{[N-(methoxycarbonyl)-L-tert-leucyl]amino}-4-(S)-hydroxy-6-phenyl-2-azahexane hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In acetone at 20 - 55℃; for 2.5h; Concentration; Solvent; Temperature;92.3%
N-benzyl-N-(tert-butoxycarbonyl)glycine
76315-01-0

N-benzyl-N-(tert-butoxycarbonyl)glycine

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-(benzyl(tert-butoxycarbonyl)amino)acetate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-(benzyl(tert-butoxycarbonyl)amino)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;89%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

atazanavir
198904-31-3

atazanavir

C54H68N6O7

C54H68N6O7

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 72h; Inert atmosphere;80%
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 72h; Inert atmosphere; Glovebox;146.1 mg
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

atazanavir
198904-31-3

atazanavir

methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-15,15-dimethyl-9-((methylthio)methoxy)-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-15,15-dimethyl-9-((methylthio)methoxy)-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions
ConditionsYield
With acetic anhydride; acetic acid at 20℃; for 48h; Inert atmosphere;79%
BOC-glycine
4530-20-5

BOC-glycine

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-((tert-butoxycarbonyl)amino)acetate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-((tert-butoxycarbonyl)amino)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere;76%
atazanavir
198904-31-3

atazanavir

(3S,8S,9S,12S)-3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyrimidinyl)phenyl]methyl]-2,5,6,10,13-pentaazatetradecanedioate dimethyl sulfate

(3S,8S,9S,12S)-3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyrimidinyl)phenyl]methyl]-2,5,6,10,13-pentaazatetradecanedioate dimethyl sulfate

Conditions
ConditionsYield
Stage #1: atazanavir In ethanol at 25 - 30℃; for 0.5h;
Stage #2: With sulfuric acid In ethanol; n-heptane; acetone at 15 - 40℃; Temperature;
75.5%
t-Boc-L-valine
13734-41-3

t-Boc-L-valine

atazanavir
198904-31-3

atazanavir

(2S,3S)-3-((S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanamido)-1-(2-((S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanoyl)-1-(4-(pyridin-2-yl)benzyl)hydrazinyl)-4-phenylbutan-2-yl (tert-butoxycarbonyl)-L-valinate

(2S,3S)-3-((S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanamido)-1-(2-((S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanoyl)-1-(4-(pyridin-2-yl)benzyl)hydrazinyl)-4-phenylbutan-2-yl (tert-butoxycarbonyl)-L-valinate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;74.1%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;74%
Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (R)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (R)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;71.2%
carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

atazanavir
198904-31-3

atazanavir

methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-9-(((1-chloroethoxy)carbonyl)oxy)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-9-(((1-chloroethoxy)carbonyl)oxy)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;70%
(S)-2-(2-N-tert-butoxycarbonylamino)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-propanoic acid
94732-15-7

(S)-2-(2-N-tert-butoxycarbonylamino)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-propanoic acid

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;67.7%
carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

atazanavir
198904-31-3

atazanavir

methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-9-(((chloromethoxy)carbonyl)oxy)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-9-(((chloromethoxy)carbonyl)oxy)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;66%
trametinib

trametinib

atazanavir
198904-31-3

atazanavir

C90H96F2N16O15

C90H96F2N16O15

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 72h; Reagent/catalyst; Inert atmosphere;65%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)propanoate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;64.4%
N-(tert-butoxycarbonyl)sarcosine
13734-36-6

N-(tert-butoxycarbonyl)sarcosine

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;64%
Dibenzyl N,N-diisopropylphosphoramidite
108549-23-1

Dibenzyl N,N-diisopropylphosphoramidite

atazanavir
198904-31-3

atazanavir

methyl ((5S,8S,9S,14S)-8-benzyl-9-((bis(benzyloxy)phosphoryl)-oxy)-5-(tert-butyl)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

methyl ((5S,8S,9S,14S)-8-benzyl-9-((bis(benzyloxy)phosphoryl)-oxy)-5-(tert-butyl)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions
ConditionsYield
Stage #1: Dibenzyl N,N-diisopropylphosphoramidite; atazanavir With 1H-tetrazole In acetonitrile at 20℃; for 8h; Inert atmosphere;
Stage #2: With dihydrogen peroxide In water; acetonitrile at 0℃; for 0.166667h;
62.4%
atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (R)-2-((tert-butoxycarbonyl)amino)propanoate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (R)-2-((tert-butoxycarbonyl)amino)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;60.3%
atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;58.1%
dimethylaminoacetic acid
1118-68-9

dimethylaminoacetic acid

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-(dimethylamino)acetate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-(dimethylamino)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;57.1%
Trimethylboroxine
823-96-1

Trimethylboroxine

atazanavir
198904-31-3

atazanavir

C40H56N6O7

C40H56N6O7

Conditions
ConditionsYield
With pentamethylcyclopentadienyl(benzene)cobalt(III) hexafluorophosphate; potassium carbonate; silver carbonate In 2-methyltetrahydrofuran at 100℃; for 16h; Inert atmosphere; Sealed tube;55%
Boc-Trp-OH
13139-14-5

Boc-Trp-OH

atazanavir
198904-31-3

atazanavir

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate

(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere;51.6%
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