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Method for split preparation of S-3,4-(methylenedioxy) mandelic acid

A technology of methylenedioxy and mandelic acid, applied in the field of separation and preparation of S-3,4-mandelic acid, which can solve the resolution of 3,4-(methylenedioxy)mandelic acid, which is rarely reported and other problems, to achieve the effect of mild conditions, high optical purity and simple operation

Inactive Publication Date: 2015-12-16
彭静
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But in current research, about 3,4-(methylenedioxy) mandelic resolution resolution report is relatively rare, so how to prepare S-3,4-(methylenedioxy) mandelic acid becomes the present invention problem to be solved

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0007] (1) Resolution of 3,4-(methylenedioxy)mandelic acid

[0008] In a 50L reactor, add 40L methanol as a solvent, 1.96KG racemic 3,4-(methylenedioxy)mandelic acid, 1.50KGS-1-phenylethylamine, start stirring, heat up, and react under reflux conditions for 1.5 hours , down to 0°C, and filtered the precipitated white solid to obtain 1.09KG of crude S-1-phenylethylamine salt of S-3,4-(methylenedioxy)mandelic acid. Add the obtained 1.09KGS-3,4-(methylenedioxy)mandelic acid S-1-phenethylamine salt into 10L of methanol solution, heat up to dissolve, wait until the solid is completely dissolved, then cool down, After cooling down to 0°C, the crystalline solid was filtered to obtain 0.98KG of refined S-1-phenylethylamine salt of S-3,4-(methylenedioxy)mandelic acid.

[0009] (2) Acid hydrolysis of salt to obtain S-3,4-(methylenedioxy)mandelic acid

[0010] Dissolve 0.98KG of S-1-phenylethylamine salt of S-3,4-(methylenedioxy)mandelic acid obtained in the previous step in 4KG of wat...

Embodiment 2

[0014] (1) Resolution of 3,4-(methylenedioxy)mandelic acid

[0015] In a 50L reactor, add 30L ethanol as a solvent, 1.96KG racemic 3,4-(methylenedioxy)mandelic acid, 2.00KGS-1-phenylethylamine, start stirring, heat up, and react under reflux conditions for 2.0 hours , down to 0°C, and filtered the precipitated white solid to obtain 1.14KG of crude S-1-phenylethylamine salt of S-3,4-(methylenedioxy)mandelic acid. Add the obtained 1.14KGS-3,4-(methylenedioxy)mandelic acid S-1-phenethylamine salt into 10L of ethanol solution, heat up to dissolve, wait until the solid is completely dissolved, then cool down, After cooling down to 0°C, the crystalline solid was filtered to obtain 1.04KG of refined S-1-phenylethylamine salt of S-3,4-(methylenedioxy)mandelic acid.

[0016] (2) Acid hydrolysis of salt to obtain S-3,4-(methylenedioxy)mandelic acid

[0017] Dissolve 1.04KG of S-1-phenylethylamine salt of S-3,4-(methylenedioxy)mandelic acid obtained in the previous step in 5KG of water...

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PUM

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Abstract

The invention discloses a method for split preparation of S-3,4-(methylenedioxy) mandelic acid. The method comprises the steps that racemic 3,4-(methylenedioxy) mandelic acid and resolving agents of S-1-phenylethylamine take a reaction to obtain S-1-phenylethylamine salts of S-3,4-(methylenedioxy) mandelic acid; the salts are subjected to acidification, organic solvent extraction and concentration to obtain S-3,4-(methylenedioxy) mandelic acid. All solutions containing S-1-phenylethylamine ingredients are subjected to alcohol removal after being mixed, and the processed solutions are subjected to alkalization, organic solvent extraction and concentration to recover the S-1-phenylethylamine. The method has the characteristics that the conditions are mild; the operation is simple; the obtained product has high yield and high optical purity; the resolving agents can be recovered and cyclically utilized, and the like. The method is particularly suitable for being used for preparing and producing the S-3,4-(methylenedioxy) mandelic acid.

Description

technical field [0001] The invention relates to a method for splitting and preparing chiral α-hydroxy carboxylic acid, in particular to a method for splitting and preparing S-3,4-(methylenedioxy)mandelic acid. Background technique [0002] 3,4-(methylenedioxy)mandelic acid, as a chiral α-hydroxy carboxylic acid, has two enantiomeric configurations, R-type and S-type, and is widely used in pharmaceutical production, asymmetric synthesis, optical resolution, etc. It has important applications in many fields. But in current research, about 3,4-(methylenedioxy) mandelic resolution report is relatively rare, so how to prepare S-3,4-(methylenedioxy) mandelic acid becomes the present invention The problem to be solved. Contents of the invention [0003] The invention adopts S-1-phenylethylamine as a resolving agent, and can successfully realize the resolution and preparation of S-3,4-(methylenedioxy)mandelic acid. The operation of the invention is as follows: (1) In methanol o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/60
CPCC07D317/60
Inventor 彭静
Owner 彭静
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