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Usage

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

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

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 
• 1497427-32-3 (S)-N-[[3-[3-fluoro-4-morpholinophenyl]-2-oxo-5-oxazolidinyl]methyl]pentanamide 
• 1497427-33-4 (S)-N-[[3-[3-fluoro-4-morpholinophenyl]-2-oxo-5-oxazolidinyl]methyl]hexanamide 
• 1497427-34-5 (S)-N-[[3-[3-fluoro-4-morpholinophenyl]-2-oxo-5-oxazolidinyl]methyl]heptanamide 
• 333753-67-6 N-[(2R)-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide 
• 1532560-87-4 (S)-N-(3-amino-2-hydroxypropyl)-3-fluoro-4-morpholinoaniline 
• 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 academic research and scientific papers

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.

A novel synthesis of oxazolidinone derivatives (A key intermediate of linezolid)

Oxazolidinone derivatives a very key intermediate of Linezolid 7(a-e) have been synthesized from 3-fluoro-4-morpholinyl aniline 2 in good yield.The structures of all the compounds were confirmed by IR, 1H NMR, 13C NMR and Mass Spectral data.

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.

Synthesis of antibiotic linezolid analogues

Several new compounds of oxazolidinone class were designed, synthesized and their analogs were evaluated for antibacterial activity against Staphylococcus aureus, Staphylococcus citreus, Proteus vulgaris, Salmonella typhimurium and Klabsiella phenumoniae. The structures of all the compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral data.

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.

NOVEL INTERMEDIATES FOR 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, the key intermediate of linezolid is prepared by a) reacting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyI aniline with potassium phthalimide; b) subjecting N-[3-pthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholinyl) aniline produced in the above step to carbonylation; and c) reacting (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidiriyl] methyl]phthalimide produced in the above step with hydrazine hydrate to produce (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl] methyl]amine.