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Studies on pyrrolidones. An improved synthesis of N ‐arylmethyl pyroglutamic acids
Author(s) -
Bourry Anne,
AkuéGédu Rufine,
Rigo Benoit,
Hénichart JeanPierre,
Sanz Gérard,
Couturier Daniel
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400606
Subject(s) - chemistry , sodium borohydride , alkylation , methanol , pyroglutamic acid , aldehyde , salt (chemistry) , glutamic acid , ethanol , solubility , organic chemistry , sodium salt , molar ratio , medicinal chemistry , catalysis , amino acid , inorganic chemistry , biochemistry
Low solubility of the aromatic aldehyde in a water/ethanol medium can prevent the sodium borohydride reductive alkylation of the sodium salt of glutamic acid. In that case, the reductive alkylation can be realized in methanol by using a triethylammonium salt. The uses of 2 molar equivalent of triethylammonium salt of glutamic acid for one molar equivalent of aldehyde strongly raise the yields. Cyclization of the N‐substituted glutamic acids obtained gives then N‐arylmethyl pyroglutamic acids in good yields.