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Prepn process of chiral 4-substituent-2-oxazolidone

An oxazolidinone and chiral technology, which is applied in the field of preparation of chiral 4-substituted-2-oxazolidinone, achieves the effects of reducing the amount of solvent, shortening the time and increasing the yield

Inactive Publication Date: 2007-03-21
上海五洲药业股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is to overcome the above disadvantages and design a method for reducing cost, reducing environmental pollution and improving product quality and yield

Method used

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  • Prepn process of chiral 4-substituent-2-oxazolidone
  • Prepn process of chiral 4-substituent-2-oxazolidone

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0021] Example 1 s-(+)-4-phenyl-2-oxazolidinone

[0022] Add 1000l of hydrofuran, 151kg (1kmol) of L-phenylglycine and 95kg of sodium borohydride (2.5kmol) into a 2000l reaction tank, a little heat will be generated, keep at 10-40°C for 4-6 hours after the addition is complete , kept stirring at this temperature for 1 hour, raised the temperature to reflux within 1 hour, refluxed at reflux temperature (about 64-66°C) for 2 hours, evaporated the hydrofuran under normal and reduced pressure, and slowly added 300l water, then add 75kg sodium hydroxide and 300l alkali aqueous solution, heat up to 98-100°C and reflux for 2 hours, after reflux, add 1400l toluene and 200l ethanol for extraction, static layering, separate at 70-80°C Remove the water layer (re-extract the water layer with 300L toluene and combine the organic layers) add 100kg of potassium carbonate to the toluene layer, add 120kg (1.1kmol) of ethyl chloroformate dropwise at 60-80°C, add dropwise for 1 hour, add dropwis...

example 2

[0035] Example 2 (R)-(-)-4-phenyl-2-oxazolidinone

[0036] In the same example 1, the starting material is changed from L-phenylglycine to D-phenylglycine. The yield is 95%, the content is over 99.9%, and the ee value is 99.9%.

example 3

[0037] Example 3 (S)-(-)-4-phenyl-2-oxazolidinone

[0038] In the same example 1, the starting material is L-phenylalanine from L-phenylglycine, the feeding amount is changed from 151kg to 165kg, and the output of the title product is 160kg-168kg. The yield is 90-95%, the content is 99.9%, and the ee value is 99.9%.

[0039] After the reduction reaction of this product, the extraction solvent is a single toluene solvent.

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PUM

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Abstract

The present invention discloses the preparation process of one kind of chiral 4-substituent-2-oxazolidone. The preparation process includes the first reducing chiral amino acid into alcohol in the presence of Lewis acid and catalyst metal boron compound, the subsequent acylation with acyl chloride compound and no phosgene, and cyclization in buffering solution with strong alkali catalyst. The present invention has low cost, less reaction steps, less wastes produced, high product quality and high total yield, and is suitable for industrial production.

Description

Technical field: [0001] The invention relates to the technical field of medicinal chemistry. It specifically relates to a preparation method of chiral 4-substituted-2-oxazolidinone. Background technique: [0002] Since the thalidomide incident occurred in the 1960s, the research on the chirality of drugs and chiral drugs has attracted the attention of countries all over the world. The traditional racemic resolution technology has greatly hindered the research and development of chiral drugs. [0003] In 1964, Mitsni used chiral adjuvant for the first time to obtain the result of stereo control of asymmetric aldol condensation reaction. Although the stereoselectivity was not high (only 58%), it caused an upsurge in chiral adjuvant research. A significant improvement occurred in the decade, when Evans and Madamune introduced a series of chiral auxiliaries leading to high stereoselectivity, including the 4-substituted-2-oxazolidinone products, which induced highly enantiosele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/20
Inventor 孙海全杨成志卢启轩张志梅许清子周萍张书桥
Owner 上海五洲药业股份有限公司
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