CAL-B-mediated efficient synthesis of a set of valuable amides by direct amidation of phenoxy- and aryl-propionic acids

Ben Amara, Nour El Houda;Merabet-Khelassi, Mounia;Aribi-Zouioueche, Louisa;Riant, Olivier
(2021) Chemical Papers — Vol. 75, n° 8, p. 4045-4053 (2021)

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Authors
  • Ben Amara, Nour El HoudaUCLouvain
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  • Merabet-Khelassi, Mouniaorcid-logo
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  • Aribi-Zouioueche, Louisaorcid-logo
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Abstract
An efficient, easy and sustainable amidation of a set of non-activated carboxylic acids with anilines, assisted by CAL-B, as biodegradable catalyst, is reported. The enzymatic amidation reactions are performed on set of nonsteroidal anti-inflammatory drugs (NSAIDs), phenoxypropionic acid and protected-prolines by direct condensation of one equivalent of carboxylic acids and two equivalents of anilines derivatives in heptane after 72 h of reaction at 80 °C. The obtained carboxylic amides are recovered with isolated chemical yields varied between moderate and excellent. Fourteen from them are reported for the first time, and an X-ray crystal is obtained for: N-(4-iodophenyl)-2-(4-isobutylphenyl)propanamide 1d.
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Ben Amara, N. E. H., Merabet-Khelassi, M., Aribi-Zouioueche, L., & Riant, O. (2021). CAL-B-mediated efficient synthesis of a set of valuable amides by direct amidation of phenoxy- and aryl-propionic acids. Chemical Papers, 75(8), 4045-4053. https://doi.org/10.1007/s11696-021-01636-5 (Original work published 2021)