Studies on pyrrolidinones. Michael reaction of glutamic acid and diethylglutamate

Abstract

Starting from glutamic acid or diethyl glutamate, some derivatives of N‐(2‐carboxyethyl), N‐(3‐oxobutyl) and N‐(2‐cyanoethyl)pyroglutamic acid were synthesized.

Novel Tricyclic Pyroglutamide Derivatives as Potent RORγt Inverse Agonists Identified using a Virtual Screening Approach

“…Alkylation of commercially available methyl or ethyl ( S )-5-oxopyrrolidine-2-carboxylate 20 by an alkyl halide followed by saponification of ester 21 provided substituted ( S )-pyroglutamic acid 22 . The N-substituted pyroglutamic acid derivatives could also be obtained by the cyclization of N-alkyl glutamate esters or N-alkylglutamic acid, − which were obtained by reductive alkylation of diethyl l -glutamate hydrochloride or l -glutamic acid with an aldehyde or ketone, or by another N-alkylation method. For example, conjugate addition of glutamic acid 23 to acrylonitrile provided 24 , which was cyclized to provide 25 .…”

An Efficient and Selective conversion of Hydrazides into Esters and Acids

“…1 Several hydrazides have been used for the synthesis of variety of heterocycles. 2 A variety of oxidising agents 3,4 have been used for the conversion of hydrazides into the corresponding acids, but with the formation of undesired side products along with the expected esters/acids. Sodium hexanitrocobaltate(III) 5 -catalysed oxidation of hydrazides leads to the formation of acyl azides rather than esters/acids.…”