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Prepn process of (R)-N-(3-fluoro-4-morpholinyl phenyl)-oxazolone-5-methyl alcohol

A technology of morpholine phenyl and preparation process is applied in the field of new synthesis process of important intermediate-N-oxazolone-5-methyl alcohol, and can solve the problem of rare raw materials, long process route and high price of the original process problem, to achieve the effect of simple process, low price and mild reaction

Inactive Publication Date: 2006-05-17
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0025] 1. The original process route is long, and there are seven steps of reaction from the starting material to the final product, and each step must go through separation, purification, drying and other processes
[0026] 2. The raw materials of the original process are rare and the price is relatively high

Method used

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  • Prepn process of (R)-N-(3-fluoro-4-morpholinyl phenyl)-oxazolone-5-methyl alcohol

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Embodiment

[0049] (1) Synthesis of 3-fluoro-4-morpholine nitrobenzene:

[0050] Dissolve 20ml 3,4-difluoronitrobenzene (0.18mol) in 50mL C 2 h 5 OH and add 0.5 g of anhydrous Na to the solution 2 CO 3 . Dissolve 19ml (0.20mol) morpholine in 50mL C 2 h 5Add the above solution after diluting with OH, and react for 6 hours under reflux (t=79°C), and the reaction solution is slightly orange-yellow. After cooling, it was filtered to obtain a yellow solid. The mother liquor was distilled to obtain a small amount of orange solid. The solid phases were combined, washed twice with 120 ml of water, and vacuum-dried for 50 min (vacuum degree 0.95, t=85° C.) to obtain 33.1 g of a yellow solid. After the above solid was recrystallized with ethyl acetate, it was stored in a dark place to prevent discoloration. The yield was 81.11%. It was observed under a microscope as a yellow flaky transparent crystal, and its melting point was mp111.7- 112.5°C. (Literature value mp 111-112°C)

[0051] Yiel...

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Abstract

The present invention discloses the preparation process of Linezolid, and the preparation process includes the following steps: condensation of morpholine and 3, 4-difluoro nitrobenzene; reduction into 3-fluoro-4-morpholinyl aniline under the catalysis of Fe, and acylation with phosgene into 3-fluoro-4-morpholinylphenyl isocyanate; cyclization with (R)-butyl glycidate to produce (R)-N-(3-fluoro-4-morpholinylphenyl)-oxazolone-5-methyl alcohol; and further conventional synthesis steps. The present invention has simple technological process, mild reaction condition, cheap catalyst and low production cost, and is favorable to industrial production.

Description

(1) Technical field [0001] The present invention relates to a new process for the preparation of pharmaceutical intermediates, specifically an important intermediate (R)-N-(3-fluoro-4-morpholine phenyl)-oxazolone-5 involved in the synthesis of antibacterial drug Linezolid - A new process for the synthesis of methyl alcohol. (2) Background technology [0002] (R)-N-(3-fluoro-4-morpholine phenyl)-oxazolone-5-methyl alcohol (hereinafter referred to as oxazolone) is a new generation of antibacterial drugs (R)-N-(3 -Fluoro-4-morpholine phenyl)-2-oxo-oxazole-5-methyl-acetamide (hereinafter referred to as Linezolid or Linezolid) is an important intermediate involved in the synthesis process. [0003] Linezolid is a newest fully synthetic chemical antibacterial drug with the chemical name (R)-N-(3-fluoro-4-morpholine phenyl)-2-oxo-oxazole-5-methyl-acetamide. It was first successfully developed by pharmacia∝Upjohn in the 1990s and approved for marketing in the United States in 2000...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12
Inventor 黄强李华牛柏林班春兰
Owner ZHENGZHOU UNIV
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