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Method for preparing inezolid

A technology of linezolid and acetamide, applied in the field of preparation of linezolid, can solve the problems of harsh reaction conditions, low yield of linezolid, complicated purification operation of intermediates, etc. Effect

Active Publication Date: 2012-07-11
广东暨大基因药物工程研究中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a preparation method of linezolid, to solve the technical problems of low yield of linezolid, complicated purification operation of intermediates and harsh reaction conditions

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0037] Preparation of 3-fluoro-4-morpholinonitrobenzene

[0038] At room temperature, morpholine (26ml, 297mmol), N,N-diisopropylethylamine (51.2ml, 293mmol), and ethyl acetate (150ml) were added into a 500ml three-necked flask. 3,4-Difluoronitrobenzene (30ml, 271mmol) was added dropwise. After dropping, stir overnight at room temperature and react for 24 hours. The next day, a TLC plate was used to determine if the reaction was complete. (The solvent system is petroleum ether:ethyl acetate=5:1). Dichloromethane (100ml), ethyl acetate (420ml), water (200ml) were added to the reaction mixture. Two-phase separation, organic phase with anhydrous MgSO 4 Let dry for 2 hours. Remove MgSO by filtration 4 . A yellow solid was obtained by rotary evaporation, and 48.9 g of a solid was obtained by vacuum drying, with a yield of 79.3%.

[0039] Synthesis of 3-Fluoro-4-Morpholinylaniline by Reduction of Hydrazine Hydrate Catalyzed by Ferric Oxyhydroxide

[0040] Step 1: Prepar...

Embodiment 2

[0061] Preparation of 3-fluoro-4-morpholinonitrobenzene

[0062]At room temperature, morpholine (52ml, 594.mmol), N,N-diisopropylethylamine (102.4ml, 586mmol), and ethyl acetate (300ml) were added into a 500ml three-necked flask. 3,4-Difluoronitrobenzene (60ml, 542mmol) was added dropwise. After dropping, stir overnight at room temperature and react for 24 hours. The next day, a TLC plate was used to determine if the reaction was complete. (The solvent system is petroleum ether:ethyl acetate=5:1). Dichloromethane (200ml), ethyl acetate (840.ml), water (400ml) were added to the reaction mixture. Two-phase separation, organic phase with anhydrous MgSO 4 Let dry for 2 hours. Remove MgSO by filtration 4 . A yellow solid was obtained by rotary evaporation, and 48.9 g of a solid was obtained by vacuum drying, with a yield of 79.3%.

[0063] Synthesis of 3-Fluoro-4-Morpholinylaniline by Reduction of Hydrazine Hydrate Catalyzed by Ferric Oxyhydroxide

[0064] Step 1: Prep...

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Abstract

The invention provides a method for preparing inezolid from N-benzyloxy-3-fluoro-4-morpholinyl aniline and S-N-(acetoxy-3-chloropropyl) acetamide through reaction. The N-benzyloxy-3-fluoro-4-morpholinyl aniline is prepared according to the following steps: (1) subjecting 3-fluoro-4-morpholinyl nitrobenzene to reduction reaction to generate 3-fluorine-4-morpholinyl aniline, and (2) subjecting the 3-fluorine-4-morpholinyl aniline to acylation reaction to generate the crude N-benzyloxy-3-fluoro-4-morpholinyl aniline, wherein the mixture of FeO(OH) and hydrazine hydrate is used as the reducing agent to carry out the reduction reaction. The prepared 3-fluorine-4-morpholinyl aniline has high yield so that the yield of the inezolid is further increased, and in addition, the prepared 3-fluorine-4-morpholinyl aniline is very easy to purify.

Description

technical field [0001] The invention relates to a preparation method of linezolid. Background technique [0002] Linezolid, the English name is linezolid, the chemical name is (S)-N-{3-[3-fluoro-4-(4-morpholinylphenyl)-2-oxo-5-oxazolinyl]methanol Base}-acetamide, the structure of which is shown below. [0003] [0004] Linezolid, the first synthetic oxazolidinone antibiotic, was launched in the United States by Pfizer in July 2000 under the trade name Zyvox. This is also the only type of chemically fully synthetic antibacterial drug with a new structure that has emerged in the past 30 years. The drug can treat nosocomial pneumonia, skin and soft tissue infection, community infectious pneumonia and other diseases, and its efficacy has been confirmed by clinical research. In addition, because linezolid selectively binds to the 50S subunit ribosome, unlike other bacterial protein synthesis inhibitors, there will be no cross-resistance effect with other bacterial protein s...

Claims

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Application Information

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IPC IPC(8): C07D263/20
Inventor 张庆华李荣东
Owner 广东暨大基因药物工程研究中心有限公司
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