Issue 9, 1986

Linear oligopeptides. Part 147. Chemical and crystallographic study of the reaction between benzyloxycarbonyl chloride and α-aminoisobutyric acid

Abstract

From the reaction mixture of benzyloxycarbonyl chloride and α-aminoisobutyric acid three crystalline compounds were isolated and characterized by chromatographic and spectroscopic techniques and X-ray diffraction. Two of them are polymorphic forms of the N-protected amino acid, which differ in the orientation of the phenyl ring relative to the urethane moiety and in the packing modes of the molecules, including the intermolecular hydrogen-bonding arrangements. The third compound is the N-protected dipeptide, the formation of which is not unexpected in the synthesis of the N-benzyloxycarbonyl amino acid derivative. The crystal structure of the symmetric carboxylic anhydride from the N-protected amino acid, a reasonable reactive intermediate in the formation of the N-protected dipeptide, is also described.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1986, 1371-1376

Linear oligopeptides. Part 147. Chemical and crystallographic study of the reaction between benzyloxycarbonyl chloride and α-aminoisobutyric acid

G. Valle, F. Formaggio, M. Crisma, G. M. Bonora, C. Toniolo, A. Bavoso, E. Benedetti, B. Di Blasio, V. Pavone and C. Pedone, J. Chem. Soc., Perkin Trans. 2, 1986, 1371 DOI: 10.1039/P29860001371

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