Open AccessMechanochemical Synthesis of Primary Amides
Author(s) -
Jorge Gómez-Carpintero,
Juan Domingo Sánchez,
Juan Francisco González,
J. Carlos Menéndez
Publication year - 2021
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c02350
Subject(s) - chemistry , dipeptide , stereocenter , primary (astronomy) , organic chemistry , ethanol , carboxamide , mechanochemistry , stereochemistry , amino acid , catalysis , enantioselective synthesis , biochemistry , physics , astronomy
Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N -BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.