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Method for preparing 4-substituted chirality oxazolidinone compounds

A technology for oxazolidinones and compounds, applied in the field of preparation of chiral 4-substituted oxazolidinones, can solve problems such as potential safety hazards, and achieve the effects of reducing waste water discharge, reducing production costs, and reducing potential safety hazards

Active Publication Date: 2008-07-30
SUQIAN KEYLAB BIOCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is: the use of phosgene in the prior art to carry out acylation to form a ring has a serious potential safety hazard. The present invention provides a preparation method without acylation process

Method used

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  • Method for preparing 4-substituted chirality oxazolidinone compounds
  • Method for preparing 4-substituted chirality oxazolidinone compounds
  • Method for preparing 4-substituted chirality oxazolidinone compounds

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0019] Example 1: Preparation of s-(+)-4-benzyl-2-oxazolidinone

[0020] Add 26.1 g (0.12 mol) of L-phenylalanine methyl ester hydrochloride to 100 ml of dichloromethane, 30.2 g (0.36 mol) of sodium bicarbonate, and dropwise add 14.3 g (0.13 mol) of methyl chloroformate at room temperature, After dripping, stir at room temperature for 6 hours, filter, recover the solvent dichloromethane, and obtain an oil Add 400ml of absolute ethanol, add 13.3g (0.12mol) of calcium chloride, 12.9g (0.24mol) of potassium borohydride, react at 15-25°C until the reduction is complete, recover the solvent ethanol, add 150ml of 1M citric acid, and use ethyl acetate The ester was extracted twice, each time the amount of extraction was 200ml, the organic layers were combined, and the solvent ethyl acetate was recovered to obtain the reduced product Add 160ml of toluene, 33g (0.24mol) of potassium carbonate, heat to reflux to separate water for 2 hours, suction filter while it is hot, cool and cry...

example 2

[0023] Example 2: Preparation of R-(-)-4-benzyl-2-oxazolidinone

[0024] D-phenylalanine methyl ester hydrochloride 26.1g (0.12mol) was added dichloromethane 100ml, sodium bicarbonate 30.2g (0.36mol), at room temperature was added dropwise ethyl chloroformate 14.3 grams (0.13mol), After dripping, stir at room temperature for 6 hours, filter, recover the solvent dichloromethane, and obtain an oil , add 400ml of absolute ethanol, add 13.3g (0.12mol) of anhydrous calcium chloride, 12.9g (0.24mol) of potassium borohydride, react at 15-25°C until the reduction is complete, recover the solvent ethanol, add 150ml of 1M citric acid, Two extractions were carried out with ethyl acetate, each time the amount of extraction was 200ml, the organic layers were combined, and the solvent ethyl acetate was recovered to obtain the reduced product. Add 160ml of toluene, 33g (0.24mol) of potassium carbonate, heat to reflux to separate water for 2 hours, suction filter while hot, crystallize the ...

example 3

[0027] Example 3: Preparation of s-(+)-4-phenyl-2-oxazolidinone

[0028] Add 100 ml of methylene chloride and 30.2 g (0.36 mol) of sodium bicarbonate to 24.4 g (0.12 mol) of L-phenylglycine methyl ester hydrochloride, add 14.3 g (0.13 mol) of ethyl chloroformate dropwise at room temperature, drop Stir at room temperature for 6 hours, filter, and recover the solvent dichloromethane to obtain off-white solid Add 400ml of absolute ethanol, add 13.3g (0.12mol) of anhydrous calcium chloride, 12.9g (0.24mol) of potassium borohydride, react at 15-25°C until the reduction is complete, recover the solvent ethanol, add 150ml of 1M citric acid, and use Ethyl acetate was extracted twice, each extraction dosage was 200ml, the organic layers were combined, and the solvent ethyl acetate was recovered to obtain the reduced product Add toluene 160ml, potassium carbonate 33g (0.24mol), heat to reflux for 2 hours, filter while hot, the filtrate is cooled and crystallized, suction filtered, an...

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Abstract

The invention relates to a preparation method of chiral 4-substituted oxazolidone, which belongs to the pharmaceutical chemistry technical field. Chiral amino acid ester or chiral amino acid ester salt is added into a solvent, supercarbonate is charged, chloro formate is titrated at the room temperature, and mixed for 5 to 8 hours at the room temperature after titration is completed, filtering is performed, and the solvent is recovered to obtain an intermediate compound a; the intermediate compound a is adopted in an anhydrous chloride solution for accelerating the catalyst of borohydride, reaction is performed for 4 to 10 hours at 0 to 40 DEG C, the solvent is recovered, a citric acid solution is added, extraction is performed by using ethyl acetate, an organic layer is combined, the solvent is recovered, and then an intermediate compound b is obtained; potassium carbonate is added into the intermediate compund b, heating, back flow and water diversion are performed for 2 to 4 hours, pump filtering is performed before cooling down, the filter liquor is cooled and recrystallized, pump filtering and drying are then performed to obtain a white crystalline solid 4-substituted chiral oxazolidone chemical compound. The invention provides the preparation method of a 4-substituted chiral oxazolidone chemical compound, the invention aims at the problem of significant safe hidden danger caused when phosgene is adopted for acidylation and cyclization in the prior art.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a method for preparing chiral 4-substituted oxazolidinones. 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 racemization resolution technology has greatly hindered the chiral drug Explore and develop. [0003] In 1964, Mitsni used chiral adjuvant for the first time to obtain the result of stereo control of asymmetric aldol condensation. Although the stereoselectivity was not high (only 58%), it caused an upsurge in chiral adjuvant research. 4-substituted Chiral oxazolidinones, [0004] [0005] Since the 1980s, it has been widely used in organic asymmetric synthesis. (Evans. D.A J. Am Chem. Soc. 1981, 1032127-2129) are thus referred to simply as Evans prosthetic groups. In the synthesis of Evans...

Claims

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Application Information

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IPC IPC(8): C07D263/20C07B53/00
Inventor 王明春印霞
Owner SUQIAN KEYLAB BIOCHEMICAL CO LTD
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