Original scientific paper

Activation of the Carboxylic Acids by Anhydride Formation with N-Acyl-N-Alkyl Carbamic Acid

Miće Kovačević ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
Jure J. Herak ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
Branimir Gašpert ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia

Abstract

The mixed anhydrides with N-acyl carbamic acid (IV) were
prepared by the reaction of carboxylic acids (Ill) with N-chlorocarbonyl
lactams (Ila) or sec. amides (lib). Decarboxylation of IV
yielded N-acyl lactams (VI), while symmetrical anhydrides (VII)
were obtained by the side reaction of IV with carboxylic acids
(III). Aminolysis of IV yielded carboxylic acid amides (IX) in high
yield and purity. IVb was used in the preparation of aminosubstituted
beta-lactam antibiotics (XII), as a new way of activating
N-protected phenylglycine (lllg), during acylation of 6-APA or
7-ADCA (XI).

Keywords

Hrčak ID:

194249

URI

https://hrcak.srce.hr/194249

Publication date:

15.4.1983.

Visits: 1.384 *