Method for preparing S-4-methoxymandelic acid through splitting S-1-phenylethylamine

A technology of methoxymandelic acid and S-4-, which is applied in the field of separation and preparation of S-4-methoxymandelic acid, can solve the problems of difficult to obtain, expensive biological resolution catalysts and chemical resolution agents, and optical purity Simple operation, mild conditions and high optical purity are achieved without high-level problems

Inactive Publication Date: 2015-12-09
彭静
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  • Application Information

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Problems solved by technology

The two reported methods have the disadvantages of low optical purity of the product, expens

Method used

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Examples

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Embodiment 1

[0007] (1) Resolution of 4-methoxymandelic acid

[0008] In a 1000ML round bottom flask, add 400ML methanol as a solvent, 18.2G racemic 4-methoxymandelic acid, 15.0G S-1-phenylethylamine, start stirring, heat up, and reflux for 2.0 hours, then cool down to 0°C , filtered the precipitated white solid to obtain 12.1G of crude S-1-phenethylamine salt of S-4-methoxymandelic acid. Add the obtained S-1-phenethylamine salt of 13.5GS-4-methoxymandelic acid into 110ML of methanol solution, heat up to dissolve, and wait for the solid to completely dissolve, then cool down to 0°C, and The crystalline solid was filtered to obtain 10.8 g of refined S-1-phenethylamine salt of S-4-methoxymandelic acid.

[0009] (2) Acid hydrolysis of salt to obtain S-4-methoxymandelic acid

[0010] Dissolve 10.8G of S-1-phenethylamine salt of S-4-methoxymandelic acid obtained in the previous step in 300ML of water, add hydrochloric acid dropwise to adjust the pH value to 4, add 100ML of dichloromethane to ...

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Abstract

The invention discloses a method for preparing S-4-methoxymandelic acid through splitting. The method concretely includes the steps that in alcohol solvent, racemic 4-methoxymandelic acid is used as a raw material, S-1-phenylethylamine is used as a splitting agent for reaction, then S-1-phenylethylamine salt of S-4-methoxymandelic acid is obtained through cooling, crystallizing and separating, and S-4-methoxymandelic acid is obtained through acid freeing after salt recrystallization is performed; after the solution containing the splitting agent is mixed, alcohol is removed through evaporation, after cooling, water and alkaline are added for freeing, and the splitting agent which is S-1-phenylethylamine is obtained through extracting, drying and concentrating. The method for preparing S-4-methoxymandelic acid through splitting has the advantages that conditions are mild, operation is easy, the product yield is good, optical purity is high, and the splitting agent can be recycled, and is quite suitable for preparing and producing S-4-methoxymandelic 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-4-methoxymandelic acid. Background technique [0002] 4-Methoxymandelic acid, as a chiral α-hydroxy carboxylic acid, has two enantiomeric configurations of R-type and S-type, and has important applications in many fields such as pharmaceutical production and asymmetric synthesis. In current reports, the methods for preparing S-4-methoxymandelic acid can be divided into asymmetric hydrolysis and chemical resolution. Asymmetric hydrolysis uses D-4-methoxymandelic acid methyl ester as a raw material to obtain S-4-methoxymandelic acid through enzyme-catalyzed asymmetric hydrolysis (Journal of the Chemical Society, p.2069-2072), while The chemical resolution method is to use (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxylamine)butane as a resolving agent to resolve 4-methoxymandelic acid to obtain S- 4-Methoxyman...

Claims

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Application Information

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IPC IPC(8): C07C59/64C07C51/487C07C51/42
CPCC07C51/487C07B57/00C07B2200/07C07C51/42C07C59/64
Inventor 彭静
Owner 彭静
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