Reaction of N-carboxy-α-amino-acid anhydrides with hydrochlorides of hydroxylamine, o-alkylhydroxylamines, and amines; syntheses of amino-hydroxamic acids, amido-oxy-peptides, and α-amino-acid amides

Yehuda Knobler, Shmuel Bittner, M. A.X. Frankel

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4 Scopus citations

Abstract

The reaction of anhydrides of N-carboxy-α-amino-acids with hydrochlorides of amines, resulting in hydrochlorides of α-amino-acid amides and derivatives, competes successfully with polymerisation of the aminoacid or with solvent interaction. The order of reactivity is the reverse of the basicity of the attacking amine. The dependence of the reaction on solvents, on temperature, on amount of acid present, and on the steric requirements of the amine, has been followed. Procedures were worked out for syntheses of: (a) amido-oxy-peptides of amino-oxyacetic acid, of canaline and its dioxopiperazine, (6) aminohydroxamic acids, and (c) N-aryl- and N-alkyl-amides of amino-acids.

Original languageEnglish
Pages (from-to)3931-3940
Number of pages10
JournalJournal of the Chemical Society
StatePublished - 1 Dec 1964
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry (all)

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