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Preparation method of linezolid

A technology of linezolid and oxazolidine, which is applied in the field of pharmacy, can solve the problems of serious environmental pollution, low yield, unfavorable industrial production of linezolid, etc.

Active Publication Date: 2013-09-25
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0031] The above-mentioned route either requires a low-temperature reaction at -78°C, or uses highly toxic phosgene, or the route is cumbersome, has low yield, high cost, and serious environmental pollution, which has certain limitations in industry and is not conducive to the development of linezolid. Industrial production

Method used

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  • Preparation method of linezolid

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Example 1. Preparation of S-1-azido-3-chloro-2-propanol:

[0049] Add S-epichlorohydrin (50g, 0.543mol) and ammonium chloride (14.5g, 0.272mol) into 200mL of ethanol and 50mL of water, stir for 5min, add sodium azide (37.1g, 0.571mol), and react at room temperature After 48 hours, distill off ethanol, add a large amount of water to dissolve the inorganic salt, extract with dichloromethane, distill off the yellow liquid S-1-azido-3-chloro-2-propanol (51.5 g, 70%).

Embodiment 2

[0050] Example 2. Preparation of 3-fluoro-4-morpholine nitrobenzene:

[0051] Morpholine (5.84mL, 0.066mol) and potassium carbonate (4.5g, 0.033mol) were added to 20mL of ethanol, and 3,4-difluoronitrobenzene (10g, 0.063mol) was added dropwise at room temperature. To reflux, the reaction was complete after 3 hours, the reaction was stopped, and a large amount of solids precipitated out at room temperature, which was added to 50 mL of water, stirred and filtered, and dried to obtain the product 3-fluoro-4-morpholine nitrobenzene (13.8 g, 97%).

Embodiment 3

[0052] The preparation of embodiment three.3-fluoro-4-morpholine aniline:

[0053] Add 3-fluoro-4-morpholine nitrobenzene (11.3 g, 0.05 mol) to a mixed solution of 23 mL of ethanol and 3 mL of water, then add ammonium chloride (1.34 g, 0.025 mol) and glacial acetic acid (1.15 mL, 0.01mol), stir and heat, add iron powder (14g, 0.25mol) in batches when the temperature reaches 70°C, reflux reaction for 3-4h after the addition is complete, the reaction is complete by TLC, stop the reaction, heat filter, filter cake with 12mL Ethanol was refluxed for 0.5h, then hot filtered, the ethanol solution was combined, activated carbon decolorized, most of the ethanol was evaporated, filtered, the filter cake was washed with a small amount of ethanol, and dried to obtain the product 3-fluoro-4-morpholineaniline (7.35g, 75 %).

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Abstract

The invention provides a preparation method of linezolid which is an antimicrobial medicament with a brand-new structure and has an obvious effect in the aspects of treating drug-resistant gram-positive bacteria and Mycobacterium tuberculosis infections. The invention relates to a synthesis method of linezolid. The method comprises the following steps: carrying out a reaction on S-epichlorohydrin and sodium azide to obtain 1-azido-3-chloro-2-propanol; cyclizing 1-azido-3-chloro-2-propanol with N-(3-fluoro-4-morpholinophenyl) urethane; and finally, reducing and acetylizing to obtain the linezolid. The method provided by the invention has the advantages of cheap-price and available raw materials, simple technology process and high product yield, provides a new way for industrial production of linezolid.

Description

Technical field: [0001] The invention relates to the field of pharmacy, in particular to a method for synthesizing medicines, in particular to a method for synthesizing linezolid. Background technique: [0002] Linezolid is the first moloxazolidinone antibacterial drug developed by Pharmacia & UpJohn. On April 18, 2000, the US FDA approved linezolid for the treatment of bacteremia caused by VRE, nosocomial pneumonia and comprehensive skin infections caused by MR2SA, and bacteremia caused by PRS. The drug shows good prospects in the treatment of multidrug-resistant Gram-positive bacteria and Mycobacterium tuberculosis infection, and is expected to become another large class of new synthetic antibacterial drugs after sulfonamides and quinolones. [0003] Linezolid, as a new oxazolidinone synthetic antibacterial drug, prevents the formation of the 70S initiation complex by binding to the 50S subunit of the ribosome and the 30S subunit, that is, blocks the synthesis of bacteria...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/20
Inventor 张益坤贾贵鹏刘志凌邹江刘蕴秀杨琰
Owner CHINA RESOURCES SAIKE PHARMA
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