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
• Article Data: 3

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

General Description

(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride is a chemical compound that is a derivative of 4-chloro-1-phenylbutan-2-ol. It is a chiral compound with two stereocenters, designated as (2S,3R). The molecule contains an amino group, a hydroxyl group, and a chlorine atom, along with a phenyl ring. (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride is often used in pharmaceutical research and may have potential therapeutic applications due to its structural features. The hydrochloride salt form of the compound allows for greater solubility in aqueous solutions, making it more suitable for pharmaceutical formulations. Further research and development of this compound may lead to its use as a drug candidate or in other related fields.

Upstream product

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

Downstream Products

• 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 
• 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 

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.

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.