198904-87-9

Basic information

• Product Name: Des-N-(methoxycarbonyl)-L-tert-leucine Atazanavir Trihydrochloride
• Synonyms: (aS,S)--Amino-a-[[1-[[4-(2-pyridinyl)phenyl]methyl]hydrazino]methyl]benzenepropanol Trihydrochloride;[S-(R*,R*)]--Amino-a-[[1-[[4-(2-pyridinyl)phenyl]methyl]hydrazino]methyl]benzenepropanol Trihydrochloride;Des-N-(methoxycarbonyl)-L-tert-leucine Atazanavir Trihydrochloride;Intermediate of Atazanavir;(αS,βS)-β-AMino-α-[[1-[[4-(2-pyridinyl)phenyl]Methyl]hydrazino]Methyl]benzenepropanol Trihydrochloride;[S-(R*,R*)]-β-AMino-α-[[1-[[4-(2-pyridinyl) phenyl]Methyl]hydrazino]Methyl]benzenepr;(alphaS,betaS)-beta-Amino-alpha-[[1-[[4-(2-pyridinyl)phenyl]methyl]hydrazinyl]methyl]benzenepropanol hydrochloride;(2R,3R)-3-aMino-4-phenyl-1-{1-[4-(pyridin-2-yl)benzyl]hydrazinyl}butan-2-ol
• CAS NO: 198904-87-9
• Molecular Formula: C22H26N4O
• Molecular Weight: 362.474
• EINECS: 1806241-263-5
• Product Categories: Amines;Chiral Reagents;Heterocycles;Inhibitors;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 198904-87-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Des-N-(methoxycarbonyl)-L-tert-leucine Atazanavir Trihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Des-N-(methoxycarbonyl)-L-tert-leucine Atazanavir Trihydrochloride(198904-87-9)
• EPA Substance Registry System: Des-N-(methoxycarbonyl)-L-tert-leucine Atazanavir Trihydrochloride(198904-87-9)

Safety Data

• Hazardous Substances Data: 198904-87-9(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

Upstream product

• 198904-86-8 1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane 
• 857904-11-1 N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine 
• 198904-85-7 N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine 
• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 
• 127406-56-8 4-(2'-pyridyl)benzaldehyde 
• 109-04-6 2-bromo-pyridine 
• 437713-03-6 methanesulfonic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-propyl ester 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 

Downstream Products

• 229975-97-7 atazanavir sulphate 
• 198904-31-3 atazanavir 

Relevant articles and documents

Process research and development for an efficient synthesis of the HIV protease inhibitor BMS-232632

Development of an efficient and scalable process for the human immunodeficiency virus (HIV) protease inhibitor BMS-232632 1-[4-(pyridin-2-yl)phenyl]-5(S)-2,5-bis{[N-(methoxycarbonyl)L-tert- leucinyl]-amino}-4(S)-hydroxy-6-phenyl-2-azahexane, is described. The key step in the synthesis of the intermediate N-1-(tert-butyloxycarbonyl)-N-2-[4-(pyridin-2-yl)benzylidene]hydrazone (11) was the Pd-mediated coupling of boronic acid 9 with 2-bromopyridine. An efficient procedure was developed for the chemoselective reduction of hydrazone 11 to hydrazine carbamate 4. The key intermediate N-(tert-butyloxycarbonyl)-2(S)-amino-1-phenyl-3(R)-3,4-epoxy-butane (6) was prepared stereoselectively from chiral diol 10. The subsequent union of 4 and 6 followed by coupling with N-methoxycarbonyl-L-tert-leucine provided the free base BMS-232632 in high yield. Evaluation of a variety of salts and identification of bisulfate salt 19 with enhanced bioavallability are also described.

PROCESS FOR THE PREPARATION OF ATAZANAVIR BISULFATE

The present invention relates to an improved process for the preparation of Atazanavir bisulfate Form A. The present invention also relates to a pharmaceutical composition using the Atazanavir bisulfate Form A of the invention.

PROCESS FOR THE PREPARATION OF ATAZANAVIR SULFATE SUBSTANTIALLY FREE OF DIASTEREOMERS

The present invention provides atazanavir sulfate substantially free of diastereomeric impurities. The present invention also provides atazanavir sulfate having D-tertiary leucine analogues less than 0.1%. The present invention further relates to an improved process for preparing atazanavir sulfate, substantially free of its diastereoisomeric impurities, which comprises of reacting diamino compound (IV) with N-methoxycarbonyl-(L)-tertiary-leucine (V) having D-isomer less than 0.1 % to obtain atazanavir base; conversion of atazanavir base to atazanavir sulfate by reacting with sulfuric acid and crystallization of atazanavir sulfate from suitable organic solvent(s).