868405-66-7

Basic information

• Product Name: 2-Propanol, 1-chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-, (2R)-
• Synonyms: N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline;N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(4-morpholinyl)aniline;N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholinyl)aniline;N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinylaniline
• CAS NO: 868405-66-7
• Molecular Formula: C13H18ClFN2O2
• Molecular Weight: 288.75
• Mol File: 868405-66-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 488.5±45.0 °C(Predicted)
• Density: 1.320±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Propanol, 1-chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propanol, 1-chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-, (2R)-(868405-66-7)
• EPA Substance Registry System: 2-Propanol, 1-chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-, (2R)-(868405-66-7)

Safety Data

• Hazardous Substances Data: 868405-66-7(Hazardous Substances Data)

Usage

Description

2-Propanol, 1-chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-, (2R)is a chemical compound that serves as an intermediate in the synthesis of N-[(2S)-3-Amino-2-hydroxypropyl]-N-[3-fluoro-4-(4-morpholinyl)phenyl] Acetamide Hydrochloride (A609075), which is a major thermal degradation product of Linezolid (L466500). It plays a crucial role in the pharmaceutical industry, particularly in the development and production of antibiotics.

Uses

Used in Pharmaceutical Industry:
2-Propanol, 1-chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-, (2R)is used as a synthetic intermediate for the production of A609075, a compound derived from Linezolid. This intermediate is essential in the development of new antibiotics and the improvement of existing ones, contributing to the fight against bacterial infections and resistance.

Upstream product

• 2689-39-6 3-fluoro-4-(4-morpholinyl)nitrobenzene 
• 369-34-6 3,4-difluoronitrobenzene 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 93246-53-8 3-fluoro-4-(morpholinyl)aniline 

Downstream Products

• 165800-03-3 linezolid 
• 168828-82-8 (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol 
• 174649-09-3 (R)-methyl methanesulfonate 
• 496031-56-2 (R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate 
• 1532560-87-4 (S)-N-(3-amino-2-hydroxypropyl)-3-fluoro-4-morpholinoaniline 
• 333753-67-6 N-[(2R)-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide 
• 1497427-34-5 (S)-N-[[3-[3-fluoro-4-morpholinophenyl]-2-oxo-5-oxazolidinyl]methyl]heptanamide 
• 1497427-33-4 (S)-N-[[3-[3-fluoro-4-morpholinophenyl]-2-oxo-5-oxazolidinyl]methyl]hexanamide 
• 1497427-32-3 (S)-N-[[3-[3-fluoro-4-morpholinophenyl]-2-oxo-5-oxazolidinyl]methyl]pentanamide 
• 168828-90-8 (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine 
• 1390617-33-0 2-benzyl-(S)-N-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]acrylamide 
• 1390617-32-9 (S)-N-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-3,4-dimethoxybenzamide 
• 1390617-37-4 5-(aminosulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxy benzamide 
• 1390617-35-2 4-amino-5-(ethylsulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxybenzamide 

Relevant articles and documents

NOVEL PROCESS FOR PREPARATION OF LINEZOLID AND ITS NOVEL INTERMEDIATES

A novel process for preparing oxazolidinone antibacterial agent Linezolid including key intermediates of oxazolidinones comprising: reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; carbonylation to form oxazolidinone derivative; acetylation of (5R)-5-(chloromethyl)-3-(3-fluoro-4-morpholinophenyl-oxazolidin-2-one with sodium acetate to get novel intermediate; hydrolysis of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl acetate; mesylation of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol; reaction of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl methane sulphonate with potassium phthalimide; hydrolysis of (S)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl phthalimide with hydrazine hydrate; acetylation of (S)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl amine with acetic anhydride yields Linezolid in high yield.

NOVEL PROCESS FOR PREPARATION OF LINEZOLID AND ITS NOVEL INTERMEDIATES

A novel process for preparing oxazolidinone antibacterial agent Linezolid including key intermediates of oxazolidinones comprising: reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; carbonylation to form oxazolidinone derivative; acetylation of (5R)-5-(chloromethyl)-3-(3-fluoro-4- morpholinophenyl-oxazolidin-2-one with sodium acetate to get novel intermediate; hydrolysis of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl acetate; mesylation of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol; reaction of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl methane sulphonate with potassium phthalimide; hydrolysis of (S)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl phthalimide with hydrazine hydrate; acetylation of (S)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl amine with acetic anhydride yields Linezolid in high yield.

Novel process for the preparation of linezolid and related compounds

The present invention provides a novel process for preparation of 5-aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus linezolid is prepared by a) reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; b) subjecting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline produced above to carbonylation; c) reacting (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone produced above with potassium phthalinide; d) reacting (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide produced above with hydrazine hydrate; and e) reacting S-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazo-lidinyl]methyl]amine produced above with acetic anhydride to produce linezolid.