FREMGANGSMAATE VED FREMSTILLING AV 1-(3-MERCAPTO-(2S)-METHYLPROPIONYL)-PYRROLIDIN-(2S9-CARBOXYLSYRE

The invention relates to a novel process for the preparation of 1-[3-mercapto-(2S)-methylpropionyl]-pyrrolidine-(2S)-carboxylic acid through the N-acylation of L-proline. According to the process of the invention L-proline is acylated with a 3-halogen-2-methylpropionyl chloride of the formula III II...

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Bibliographic Details
Main Authors BAKONYI, ANNA, ROZSA, LASZLO, FISCHER, JANOS, FAZEKAS, GABOR, VAGO, PAL
Format Patent
LanguageNorwegian
Published 20.05.1986
Edition4
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
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Summary:The invention relates to a novel process for the preparation of 1-[3-mercapto-(2S)-methylpropionyl]-pyrrolidine-(2S)-carboxylic acid through the N-acylation of L-proline. According to the process of the invention L-proline is acylated with a 3-halogen-2-methylpropionyl chloride of the formula III III wherein Hal is a halogen atom, preferably chlorine or bromine, the obtained 1-[3-halogen-(2S)-methylpropionyl]-pyrrolidine-(2S)-carboxylic acid, wherein Hal is as stated above, is reacted with an alkali thiosulfate or alkali trithiocarbonate and the reaction product is hydrolized with an acid. The process of the invention is very economical as compared with the known processes. The desired product is prepared from methacrylic acid in 4 reaction steps with a total yield of 25 percent and from L-proline in 2 reaction steps with a total yield of 30 percent.
Bibliography:Application Number: NO19800003939