Absolute configuration of the enantiomers of 7-chloro-4-[[4-(diethylamino)-1-methylbutyl] amino] quinoline (chloroquine)

…, HN Bhargava, ET Everhart, B LaBelle…

Index: Craig; Bhargava; Everhart; LaBelle; Ohnsorge; Webster Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1167 - 1170

Full Text: HTML

Citation Number: 50

Abstract

(R)-(-)-4-[[4-(Diethylamino)-l-methylbutyl] amino]-7-chloroquinoline [(R)-(-)-chloroquine] was prepared in a 10-step synthesis starting from L-glutamic acid via NJV-phthaloyl-L-glutamic acid, NrJVy-diethyl-N", N"-phthaloyl-L-glutamine, and NJV-diethyl-L-glutamine. Reductive conversion of the a-carboxyl group to a methyl group led to R-(-)-4-amino-l-(diethylamino) pentane of> 90% optical purity, which on condensation with 4, 7-dichloroquinoline gave ( ...