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Method for preparing R-chloromandelic acid

A technology of o-chloromandelic acid and hydrochloric acid, applied in directions such as carboxylate preparation, carboxylate preparation, organic compound preparation, etc., can solve problems such as being difficult to industrialized production, and achieve the effects of easy recovery, simple operation and mild conditions

Inactive Publication Date: 2015-11-25
彭静
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many kinds of resolution methods of o-chloromandelic acid reported at present, among which electrochemical method, extraction resolution method, chromatographic resolution method, electrophoretic resolution method, and enzymatic resolution method are due to reasons such as resolution scale and resolution efficiency, Difficult to achieve industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] (1) Resolution of o-chloromandelic acid

[0014] In a 50L reactor, add 15L methanol and 15L water to prepare the solvent required for the reaction. Then add 1.87KG racemic o-chloromandelic acid in the kettle, start stirring and heat up. Under the condition of reflux, 1.80KG of R-1-naphthylethylamine was added dropwise to the system. After the dropwise addition was completed, react under reflux conditions for 1.0 hour, then cool down to room temperature, and filter the precipitated white solid to obtain 1.61KG of crude R-1-naphthylethylamine salt of R-o-chloromandelic acid. Add the obtained 1.61KGR-o-chloromandelic acid R-1-naphthylethylamine salt into 15L of methanol solution, heat up to dissolve, wait for the solid to completely dissolve, then cool down, and after cooling down to room temperature, filter the crystalline solid , 1.42KG of R-1-naphthylethylamine salt of R-o-chloromandelic acid after refining was obtained.

[0015] (2) Acid hydrolysis of salt to obtain...

Embodiment 2

[0020] (1) Resolution of o-chloromandelic acid

[0021] In a 50L reactor, add 10L ethanol and 20L water to prepare the solvent required for the reaction. Then add 1.87KG racemic o-chloromandelic acid in the kettle, start stirring and heat up. Under the condition of reflux, 1.80KG of R-1-naphthylethylamine was added dropwise to the system. After the dropwise addition was completed, react under reflux conditions for 1 hour, cool down to room temperature, and filter the precipitated white solid to obtain 1.56 KG of crude R-1-naphthylethylamine salt of R-o-chloromandelic acid. Add the obtained R-1-naphthylethylamine salt of 1.56KGR-o-chloromandelic acid into 15L of ethanol solution, heat up to dissolve, wait for the solid to completely dissolve, then cool down, and after cooling down to room temperature, filter the crystalline solid , 1.40KG of R-1-naphthylethylamine salt of R-o-chloromandelic acid after refining was obtained.

[0022] (2) Acid hydrolysis of salt to obtain R-o-...

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Abstract

The invention discloses a method for preparing R-chloromandelic acid through resolution with R-(+)-1-(1-naphthyl)ethylamine used as a chiral resolution agent. Chloromandelic acid reacts with the resolution agent R-(+)-1-(1-naphthyl)ethylamine in a corresponding solvent to produce R-(+)-1-(1-naphthyl)ethylamine salt of the chloromandelic acid, the R-(+)-1-(1-naphthyl)ethylamine salt of the R-chloromandelic acid can be obtained through crystal separation, and the R-chloromandelic acid can be obtained through acidizing; the resolution agent R-(+)-1-(1-naphthyl)ethylamine can be recovered through reaction residual solution alkali treatment. The method has the characteristics that conditions are mild, the operation is simple, the product yield is high, and the optical purity is high, besides, the resolution agent can be recycled and is extremely suitable for industrial production of the R-chloromandelic acid.

Description

technical field [0001] The invention relates to a method for preparing chiral compounds by chemical resolution, in particular to a method for preparing R-o-chloromandelic acid by using R-1-naphthylethylamine as a resolving agent. Background technique [0002] O-chloromandelic acid has two enantiomeric configurations of R-type and S-type, and is widely used in many fields such as pharmaceutical production, asymmetric synthesis, and optical resolution. Among them, R-type o-chloromandelic acid is an important intermediate of clopidogrel, a new safe and efficient anti-platelet aggregation drug. Clopidogrel is widely used clinically to prevent cardiovascular and cerebrovascular diseases such as myocardial infarction, stroke, and arteriosclerosis. Compared with several other widely used platelet inhibitors such as aspirin and ticlopidine, it has stronger effect, higher tolerance and less side effects. It is the antithrombotic drug with the highest market share. [0003] As an i...

Claims

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Application Information

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IPC IPC(8): C07C59/56C07C51/42C07C51/50
CPCC07C51/412C07B57/00C07C51/02C07C51/43C07C209/00C07C59/56C07C211/30
Inventor 彭静
Owner 彭静
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