ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Nourelhouda Benamara, Mounia Merabet-Khelassi, Louisa Aribi-Zouioueche, and Olivier Riant

Ecocompatible Asymmetric Catalysis Laboratory (L.C.A.E), Badji Mokhtar Annaba-University, Annaba, Algeria

E-mail: mounia.merabet@gmail.com

Received: 7 November 2020  Accepted: 31 March 2021

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.

Keywords: CAL-B; NSAIDs prodrugs; Boc-proline; Direct amidation

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01636-5

Chemical Papers 75 (8) 4045–4053 (2021)