369362-96-9

Basic information

• Product Name: (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride
• Synonyms: (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride
• CAS NO: 369362-96-9
• Molecular Weight: 236.141
• Mol File: 369362-96-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride(369362-96-9)
• EPA Substance Registry System: (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride(369362-96-9)

Safety Data

• Hazardous Substances Data: 369362-96-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride serves as an important compound in pharmaceutical research due to its unique structural features. Its potential therapeutic applications are being explored, with the aim of developing it into a drug candidate for various medical conditions.
Used in Drug Formulation:
The hydrochloride salt form of (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol increases its solubility in aqueous solutions, making it more suitable for the development of pharmaceutical formulations. This improved solubility can facilitate the compound's absorption and distribution within the body, which is crucial for its effectiveness as a therapeutic agent.

Upstream product

• 162536-40-5 (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane 

Downstream Products

• 165727-45-7 tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 162536-40-5 (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane 
• 1192510-20-5 methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate 
• 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 
• 198904-31-3 atazanavir 
• 229975-97-7 atazanavir sulphate 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF ATAZANAVIR OR ITS BISULFATE SALT

The present invention relates to an improved process for the preparation of atazanavir bisulfate, an inhibitor of retroviral aspartate protease. The process of the present invention comprises conversion of 1,1-dimethylethyl[(2S,3R)-4-chloro-3-hydroxy-phenylbutan-2-yl]carbamate (Formula II) into 1-[4-(pyridine-2-yl)-phenyl]-4(S)-5 hydroxy-2-N-tert-butoxycarbonylamino-5(S)—N—(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane (Formula VII) without isolating intermediate compounds formed therein, followed by its subsequent conversion to atazanavir or its bisulfate salt.

PROCESS FOR PREPARATION OF ATAZANAVIR OR ITS BISULFATE SALT

The present invention relates to an improved process for the preparation of atazanavir bisulfate, an inhibitor of retroviral aspartate protease. The process of the present invention comprises conversion of 1,1-dimethylethyl[(2S,3R)-4-chloro-3-hydroxy- -phenylbutan-2-yl]carbamate (Formula II) into 1-[4-(pyridine-2-yl)-phenyl]-4(S)-5 hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert- leucyl)amino-6-phenyl-2-azahexane (Formula VII) without isolating intermediate compounds formed therein, followed by its subsequent conversion to atazanavir or its bisulfate salt.

Production method of aminochlorohydrin sulfate

Highly pure (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane or (2S,3R)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane may be conveniently produced in high yield by: (a) reacting compound (1) with lithiumchloromethane to give compound (2) and at least a byproduct; (b) dissolving compound (2) and the byproduct in a polar solvent and adding water to the solution to precipitate compound (2) as crystals; (c) reducing the crystals of compound (2) to give compound (3) and at least its diastereomer as an impurity; (d) adding sulfuric acid thereto to give compound (4) and at least its diastereomer as an impurity; and (e) precipitating compound (4) as crystals from a solution containing acetic acid ester or acetic acid ester.