Synthesis of a trisubstituted 1, 4-diazepin-3-one-based dipeptidomimetic as a novel molecular scaffold

…, M Pellegrini, DF Mierke, M Chorev

Index: Weitz, Iris S.; Pellegrini, Maria; Mierke, Dale F.; Chorev, Michael Journal of Organic Chemistry, 1997 , vol. 62, # 8 p. 2527 - 2534

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Citation Number: 28

Abstract

We describe two routes for the synthesis of a trisubstituted 1, 2, 5-hexahydro-3-oxo-1 H-1, 4- diazepine ring (DAP), a novel, conformationally constrained, seven-membered dipeptidomimetic ring system. The linear precursor for the model DAPs, targeted for conformational analysis studies, was obtained by reductive alkylation of tert-butyl alaninate or phenylalaninate by N-Boc-α-amino-γ-oxo-N, N-dimethylbutyramide. Acetylation of the ...