Mechanochemical Synthesis of Primary Amides
Author(s) -
Jorge Gómez-Carpintero,
J. Domingo Sánchez,
Juan F. González,
J. Carlos Menéndez
Publication year - 2021
Publication title -
the 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) - stereocenter , primary (astronomy) , dipeptide , chemistry , organic chemistry , mechanochemistry , ethanol , amino acid , catalysis , biochemistry , enantioselective synthesis , 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.
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