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Method for preparing linezolid

A technology of linezolid and compounds, applied in the field of drug synthesis

Inactive Publication Date: 2013-01-02
袁建勇 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Compared with other synthetic routes reported in patents, this route is simpler, but because the side chain oxazolidinone is an achiral compound, and linezolid itself is a chiral compound, the product needs to be resolved, which can only be theoretically get half the product

Method used

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  • Method for preparing linezolid
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  • Method for preparing linezolid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The purified CuI (0.22mmol, 42mg), anhydrous K 2 CO 3 (7.35mmol, 1.02g), 3-fluoro-4-morpholinyl bromobenzene (4.41mmol, 1.15g) and acetyloxazolidinone (4.41mmol, 0.70g) were put into a 50mL two-mouth round bottom with a condenser In the flask. Vacuum and flush the bottle three times with nitrogen, and protect with nitrogen. A solution of (±)-1,2-cyclohexanediamine (0.22 mmol, 25 mg) in 1,4-dioxane (10 mL) was added via a syringe, and then stirred at 110°C for 20 hours. The reaction was cooled to room temperature and filtered through celite, then washed with dichloromethane (2×50 mL). The organic layers were combined, and the residue was separated and purified by silica gel column after concentration. The eluent is ethyl acetate: petroleum ether (60-90℃) (2:1) to obtain (S)-N-[[3-(3-fluoro-4-morpholinyl)phenyl]-2- Oxo-5-oxazolidinyl]methyl]acetamide 1.31 g (88%).

Embodiment 2

[0024] The purified CuI (0.22mmol, 42mg), anhydrous K 2 CO 3 (7.35mmol, 1.02g), 3-fluoro-4-morpholinyl bromobenzene (4.41mmol, 1.15g) and oxazolidinone (4.41mmol, 0.51g) were put into a 50mL two-necked round bottom flask with a condenser in. Vacuum and flush the bottle three times with nitrogen, and protect with nitrogen. A solution of (±)-1,2-cyclohexanediamine (0.22 mmol, 25 mg) in 1,4-dioxane (10 mL) was added via a syringe, and then stirred at 110°C for 20 hours. The reaction was cooled to room temperature and filtered through celite, then washed with dichloromethane (2×50 mL). The organic layers were combined, and the residue was separated and purified by silica gel column after concentration. The eluent is ethyl acetate: petroleum ether (60-90℃) (1:4) to obtain (S)-N-[3-(3-fluoro-4-morpholinyl)phenyl]-2-oxy Sulfo-5-oxazolidinyl]methylamine 0.81 g (62%).

Embodiment 3

[0026] The purified CuI (0.22mmol, 42mg), anhydrous K 2 CO 3 (7.35mmol, 1.02g), 3-fluoro-4-morpholinyl bromobenzene (4.41mmol, 1.15g) and benzyloxazolidinone (4.41mmol, 0.91g) were put into a 50mL two-mouth circle with a condenser Bottom flask. Vacuum and flush the bottle three times with nitrogen, and protect with nitrogen. A solution of (±)-1,2-cyclohexanediamine (0.22 mmol, 25 mg) in 1,4-dioxane (10 mL) was added via a syringe, and then stirred at 110°C for 20 hours. The reaction was cooled to room temperature and filtered through celite, then washed with dichloromethane (2×50 mL). The organic layers were combined, and the residue was separated and purified by silica gel column after concentration. The eluent is ethyl acetate: petroleum ether (60-90℃) (3:1) to obtain (S)-N-[3-(3-fluoro-4-morpholinyl)phenyl]-2-oxo (5-oxazolidinyl]methylamine 1.10g (65%).

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Abstract

The invention relates to a method for preparing linezolid. The method is characterized by reacting 3-fluoro-4-morpholinyl bromobenzene as raw material with a chiral oxazolidinone compound under the action of a catalyst to obtain linezolid. Compared with the prior art, the inventive method has the advantages of simple synthesis path, simple operation, less pollution and stable yield.

Description

Technical field [0001] The invention relates to the field of drug synthesis, in particular to linezolid ([(S)-N-[[3-(3-fluoro-4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl ]Methyl]acetamide] preparation method. Background technique [0002] Linezolid is an antibacterial agent, its chemical name is [(S)-N-[[3-(3-fluoro-4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl ]Methyl]acetamide] is an antibacterial agent, the experimental formula is C 16 H 20 FN 3 O 4 , CAS number is 165800-03-3, the structure is as follows (I): [0003] [0004] US Patent US5688792, European Patent EP717738, Israeli Patent No. 110802, Canadian Patent No. 2168560, International Patent Nos. WO95 / 07271, WO200509353 and WO20066008754 respectively disclose methods for preparing linezolid. [0005] Relatively speaking, the preparation method of ORGANIC LETTERS 2003 Vol. 5 Issue 7 963~965 is relatively simple: [0006] [0007] This route is simpler than other synthetic routes reported in patents, but because the side chain ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/20
Inventor 袁建勇李雁武
Owner 袁建勇
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