Resolution method and intermediate of cis-1-hydroxy-[1,1′-bis(cyclohexyl)]-2-carboxylic acid

A hydroxyl and formic acid technology, applied in the separation/purification of carboxylic acid compounds, chemical instruments and methods, preparation of carboxylate salts, etc., can solve the problem of expensive resolving agents, low quinine resolution yield, and inconsistent with green chemistry and other problems, to achieve the effect of low process cost and low price
CN108069846BActive Publication Date: 2020-11-03SHANGHAI INST OF PHARMA IND CO LTD +1
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
SHANGHAI INST OF PHARMA IND CO LTD
Publication Date
2020-11-03

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Abstract

The invention discloses a method for splitting cis-1-hydroxy-[1,1'-bi(cyclohexyl)]-2-formic acid and an intermediate. The method is characterized in that S-(-)-alpha-phenylethylamine or R-(+)-alpha-phenylethylamine is taken as a splitting agent for splitting the cis-1-hydroxy-[1,1'-bi(cyclohexyl)]-2-formic acid to obtain S-(-)-alpha-phenylethylamine salt of (1S, 2S)-1-hydroxy-[1,1'-bi(cyclohexyl)]-2-formic acid and R-(+)-alpha phenylethylamine salt of (1R, 2R)-1-hydroxy-[1,1'-bi(cyclohexyl)]-2-formic acid; high-pressure hydrogenation of a benzene ring and catalyzation of precious metal are avoided in the conventional preparation of rociverine single isomer. The S-(-)-alpha-phenylethylamine salt and the R-(+)-alpha phenylethylamine salt have the advantages of low cost, low process cost, environmental friendliness and suitability for industrial production.
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Description

technical field

[0001] The invention relates to a resolution method and an intermediate of cis-1-hydroxyl-[1,1'-bis(cyclohexyl)]-2-carboxylic acid. Background technique

[0002] Rociverine is an M-cholinergic receptor antagonist developed by Laboratori Guidotti S.p.A., a subsidiary of Italy's Menarini Group. It is mainly used clinically to treat gastrointestinal muscle spasm Acute and subacute abdominal pain, spasmolysis and analgesia of genitourinary tract and biliary tract, dynamic dystocia, etc. Rosiverine is marketed as a racemate, comprising four stereoisomers with the hydroxyl and ester groups in cis. In order to meet the requirements for drug application and registration, the ratio and configuration of each stereoisomer need to be confirmed. The synthesis and preparation of a single isomer of rosivirine will provide a reference for the quality research of rosivirine stereoisomer components.

[0003] Cis-1-hydroxyl-[1,1'-bis(cyclohexyl)]-2-carboxylic acid is the race...

Claims

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