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 
• 75-36-5 acetyl chloride 
• 168828-90-8 (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine 
• 1088111-01-6 (S)-3-(3-fluoro-4-(morpholino)phenyl)-5-(2-(hydroxyimino)propyl)oxazolidin-2-one 
• 530-62-1 1,1'-carbonyldiimidazole 
• 93246-53-8 3-fluoro-4-(morpholinyl)aniline 
• 161596-47-0 (S)-N-glycidylphthalimide 
• 565176-83-2 N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline 
• 183905-31-9 N-[(2S)-2-acetoxy-3-chloropropyl]acetamide 
• 79-22-1 methyl chloroformate 
• 507-09-5 tiolacetic acid 
• 224323-49-3 N-[(2S)oxiranylmethyl]acetamide 
• 212325-40-1 methyl-(3-fluoro-4-morpholinophenyl)carbamate 

Downstream Products

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

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.

Linezolid preparation method and linezolid refining method

The invention provides a linezolid preparation method, which comprises: hydrogenation reduction, amino protection and reduction reaction. The invention further provides a linezolid refining method, which comprises: purifying, refining, crystal transformation, impurity removal and other processes. According to the present invention, the reaction of the linezolid synthesis process is simple, the reagent used in the reaction is safe and non-toxic, the reaction yield is high, and the purification process of the refining method is simple, and does not require complicated chromatographic purification; and the linezolid preparation method and the refining method are suitable for large-scale industrial production.