224323-50-6

Basic information

• Product Name: linezolid
• Synonyms: Acetamide, N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- (9CI);Racemic Linezolid
• CAS NO: 224323-50-6
• Molecular Formula: C16H20 F N3 O4
• Molecular Weight: 337.35
• Mol File: 224323-50-6.mol
• Article Data: 104

Chemical Properties

• Appearance: /
• CAS DataBase Reference: linezolid(CAS DataBase Reference)
• NIST Chemistry Reference: linezolid(224323-50-6)
• EPA Substance Registry System: linezolid(224323-50-6)

Safety Data

• Hazardous Substances Data: 224323-50-6(Hazardous Substances Data)

Usage

Uses

(±)-Linezolid can be used to treat cancer.

Upstream product

• 108-24-7 acetic anhydride 
• 168828-84-0 (R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one 
• 168828-89-5 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione 
• 1373348-81-2 (S)-3-azido-1-chloropropan-2-yl 3-fluoro-4-morpholinophenylcarbamate 
• 1373348-82-3 (S)-3-Chloro-1-(1,3-dioxoisoindolin-2-yl)propan-2-yl-3-fluoro-4-morpholinophenylcarbamate 
• 224323-47-1 (S)-N-(3-chloro-2-hydroxy-1-propyl)acetamide 
• 1402550-23-5 (S)-N-(3-chloro-2-methoxycarbonyloxy-1-propyl)acetamide 
• 93246-53-8 3-fluoro-4-(morpholinyl)aniline 
• 1402550-24-6 (S)-N-(3-chloro-2-ethoxycarbonyloxy-1-propyl)acetamide 
• 1402550-26-8 (S)-N-(3-chloro-2-benzyloxycarbonyloxy-1-propyl)acetamide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 333753-67-6 N-[(2R)-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide 
• 333753-67-6 (dl)-N-[3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide 
• 79-22-1 methyl chloroformate 

Downstream Products

• 1097835-43-2 (S)-3-[3'-methoxy-4'-(N-morpholino)phenyl]-5-(N-acetamidomethyl)-oxazolidin-2-one 
• 556801-15-1 (S)-3-(4'-N-morpholinophenyl)-5-(N-acetamidomethyl)-oxazolidin-2-one 
• 1097835-42-1 C₁₆H₁₉N₃O₄ 
• 1097835-49-8 3'-d (S)-3-(4'-N-morpholinophenyl)-5-(N-acetamidomethyl)oxazolidin-2-one 
• 168828-90-8 (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine 

Relevant articles and documents

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

The human drugs - the antibiotic linezolid (1) and the anticoagulant rivaroxaban (2) - belong among modern pharmaceutics, which contain an oxazolidine-2-one moiety bearing a stereogenic center. The chirality of these drugs is a fundamental attribute for their biological activity. Herein, one of the efficient asymmetric syntheses of these drugs was studied in detail. Highly enantioselective catalysts were tested in the key step of the synthetic procedure, i.e., the asymmetric Henry reaction, under different reaction conditions, using several starting aldehydes. The corresponding nitroaldols as chiral intermediates in the syntheses of these drugs were obtained in high yields and enantiomeric excesses of up to 91% ee.

Industrial production method of linezolid

The invention belongs to the field of medicinal chemistry, and relates to an industrial production method of linezolid. A compound I and a compound II are used as initial raw materials, and linezolid is generated through cyclization and acylation reactions. The preparation method of linezolid has the advantages of simple steps, mild reaction conditions, short reaction time, cheap and easily available raw materials, safe and economic reagents, low equipment requirements and high purity of the final product, and is suitable for industrial production. A reaction formula is defined in the specification.

New linezolid synthesis method

The invention belongs to the field of organic synthesis, and particularly relates to a new linezolid synthesis method, which comprises: synthesizing 3-fluoro-4-morpholinophenyl isocyanate by using 3,4-difluoronitrobenzene as a starting raw material, carrying out cyclization on the 3-fluoro-4-morpholinophenyl isocyanate and (R)-epichlorohydrin under the catalysis of MgI2 or MgBr2 in the absence ofa solvent to obtain (R)-3-fluoro-4-morpholinophenyl oxazolidone, and carrying out azide group substitution, reduction and acetylation to obtain linezolid. According to the present invention, by usingthe new linezolid synthesis method, the reaction rate can be significantly accelerated, the yield can be increased, the cost can be reduced, the environment can be protected, the operation is simple,the post-treatment is convenient, and the method is suitable for industrial production.