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Exploration of lipase-catalyzed direct amidation of free carboxylic acids with ammonia in organic solvents

✍ Scribed by Mike J.J. Litjens; Adrie J.J. Straathof; Jaap A. Jongejan; Joseph J. Heijnen

Book ID
104209634
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
550 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Lipase-catalyzed direct amidation of free carboxylic acids is possible with ammonia in organic solvents. For butyric acid as a model compound the reaction proceeds well despite precipitation of ammonium butyrate, provided that the added molar amounts of butyric acid and ammonia are in the same range. The addition of ammonium salts is a convenient way to ensure suitable ammonia concentrations. Using Candida antarctica lipase B as the biocatalyst, the amidation proceeds well for various carboxylic acids and is very enantioselective in the amidation of 4-methyloctanoic acid.

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## Abstract The first straightforward lipase‐catalyzed enantioselective access to enantiomerically enriched tiaprofenic acid as a versatile method in chiral separation of racemates is demonstrated. The latter was directly monitored by enantioselective HPLC using a 3,5‐dimethylphenylcarbamate deriva