Original scientific paper

Preparation and lsomerization of 3S-Benzylpenicilloamides

J . J . Herak ; Research Department, Pliva Pharmaceutical and Chemical Works, Zagreb, Croatia, Yugoslavia
M. Kovačević ; Research Department, Pliva Pharmaceutical and Chemical Works, Zagreb, Croatia, Yugoslavia
B. Gašpert ; Research Department, Pliva Pharmaceutical and Chemical Works, Zagreb, Croatia, Yugoslavia

Abstract

The isomerization of 3S-benzylpenicillobenzylamide in aprotic
solvents was studied by using 1H NMR spectroscopy. The lack of
isomerization of the N-acetyl derivative of I indicated that the epimerization
at C-5 and C-6 positipn2 proceeded through the open
chain imine tautomer (III) of I or II. Since the isomerization at the
C-6 position occurred after the opening of the thiazolidine ring,
it was concluded that isomerization at this centre preceeded through
penamaldic acid (IV) as an intermediate. All four isomers· of 3S-
benzylpenicillobenzylamide were prepared and isolated as methyl
esters (II).

Keywords

Hrčak ID:

195951

URI

https://hrcak.srce.hr/195951

Publication date:

22.12.1978.

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