Tetrahedron letters

N-alkylation of pyridylalanine and pyridinecarboxylic acids and their use in synthesis of GnRH antagonists

…, Z Tian, M Kowalczuk, P Edwards, RW Roeske

Index: Zhang, Yongliang; Tian, Zhenping; Kowalczuk, Maria; Edwards, Patrick; Roeske, Roger W. Tetrahedron Letters, 1993 , vol. 34, # 23 p. 3659 - 3662

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Citation Number: 13

Abstract

Abstract A mild N-alkylation method has been developed for the synthesis of N-alkylated pyridiniumcarboxylic acids, using Ag 2 OH 2 O catalysis to enhance the low-reactivity of pyridinecarboxylic acids. Two approaches were undertaken for the synthesis of a series of GnRH antagonists containing pyridinium moieties at the side chain:(1) incorporation of Npy- alkylated D-pyridylalanine during solid phase peptide chain assembly, and (2) coupling of ...