Studies on pyrrolidones. An improved synthesis of N-arylmethyl pyroglutamic acids

✍ Scribed by Anne Bourry; Rufine Akué-Gédu; Benoit Rigo; Jean-Pierre Hénichart; Gérard Sanz; Daniel Couturier

• Book ID: 102341906
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 62 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400606

✦ Synopsis

Abstract

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.