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Resolution of 7-chloro-4(4′-diethylamino-1′methylbutyl)aminoquinoline (chloroquine) into its enantiomers

✍ Scribed by Dr. J. Cymerman Craiga; Aslam M. Ansari

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
300 KB
Volume
5
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

Evidence is accumulating that 7‐chloro‐4‐[4‐diethylamino‐1‐methylbutyl] amino quinoline (chloroquine) displays considerable stereoselectivity in its metabolism, pharmacokinetics, macromolecular interactions, and biological activity. The availability of the enantiomers has been hampered by the failure of direct methods of resolution. We now describe a successful resolution in which the atropisomeric 1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate is used in a 1:1 ratio to form stereoselectively the 2:1 diastereomeric salt from one enantiomer of the base, leaving the other in solution. By this means both enantiomers of chloroquine may be readily isolated. © 1993 Wiley‐Liss, Inc.

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The absolute configuration of the enantiomers of 6-chloro-9-(4′-diethylamino-1′-methylbutyl)-amino-2-methoxyacridine (quinacrine)
✍ J. Cymerman Craig; Bruce Labelle; Ulrich Ohnsorge 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 176 KB

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