Sy. Ambekar et Dc. Gowda, SYNTHESIS OF HETEROBIFUNCTIONAL CROSS-LINKING REAGENTS - OMEGA-(N-MALEIMIDO)ALKANOIC ACID HYDRAZIDES, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 35(3), 1996, pp. 184-186
omega-(N-Maleimido)alkanoic acid hydrazides (6a-c) with C-11, C-7 and
C-5 alkyl arms have been synthesized by novel method. Tile method invo
lves tile reaction between maleic anhydride and omega-aminoalkanoic ac
ids (2) to get maleamic acids (3) which are in turn cyclized to omega-
(N-maleimido)alkanoic acids (4) using fused sodium acetate and acetic
anhydride. These maleimidoalkanoic acids are activated and then conver
ted in situ into their N-2-t-Lutyloxycarbonyl hydrazides (5) from whic
h the t-butyl-based protecting group is cleaved without damage to the
maleimide moiety to obtain the title compounds.