Synthesis of New Racemic α,α-Diaminocarboxylic Ester Derivatives

Abstract

New racemic methyl or ethyl α-aminoglycinate derivatives were synthesized by N-alkylation of amines (aniline, 4-methylaniline, 2-methylaniline, 2,4-dimethoxyaniline, 2-nitroaniline, 4-chloro-2-fluoroaniline, 2-naphthylamine, benzylamine, N,N-dibenzylamine, and cyclohexylamine) with methyl or ethyl α-azidoglycinate.

Methyl 2-Benzamido-2-(1H-benzimidazol-1-ylmethoxy)acetate

“…Comparing these results with the work done by our team [12,15,16], we see that we have obtained almost the same results.…”

“…Following the research done on the synthesis of new α-carboxylic aminoesters [12] and in the synthesis of heterocyclic systems of benzimidazole derivatives, we reported in this paper another part OPEN ACCESS M777 (Page 2) of our investigations concerning the preparation of methyl 2-benzamido-2-(1H-benzimidazol-1ylmethoxy)acetate. Our strategy is based on the O-alkylation of methyl α-azido glycinate N-benzoylated with 1H-benzimidazol-1-ylmethanol.…”

Diamine Synthesis via the Nitrogen-Directed Azidation of σ- and π-C–C Bonds

“…Among recent efforts in ring-opening reactions of aminocyclopropanes and aminocycylobutanes, , our group and others have used oxidative ring-opening to access multifunctionalized building blocks. − For extending this strategy to the diazidation of aminocyclopropanes, two challenges needed to be considered: 1) the choice of a catalyst to promote both oxidative ring-opening and azide transfer; 2) the functionalization of α-azido amides by carbon nucleophiles, which was unprecedented. Indeed, only three examples using thiophenol, amine, and silyl hydride as heteronucleophiles have been reported.…”

“…29−35 For extending this strategy to the diazidation of aminocyclopropanes, two challenges needed to be considered: 1) the choice of a catalyst to promote both oxidative ring-opening and azide transfer; 2) the functionalization of α-azido amides by carbon nucleophiles, which was unprecedented. Indeed, only three examples using thiophenol, 36 amine, 37 and silyl hydride 10 as heteronucleophiles have been reported.…”

Synthesis, characterization and antibacterial activity of Methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo- 1-phenylethyl]amino}acetate

“…In continuation of our ongoing research 7,8 , this work deals to describe the synthesis and design of the methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo-1-phenylethyl]amino}acetate 2. This latter was obtained through N-alkylation of methyl -azido glycinate N-benzoylated 1 by methyl 2-amino-2-phenylacetate.…”