Synthesis of a chiral macrocyclic dibenzodicyclohexanotetraamide-containing stationary phase for liquid chromatography

✍ Scribed by Kejiang Hu; Jerald S. Bradshaw; N. Kent Dalley; Krzysztof E. Krakowiak; Naijun Wu; Milton L. Lee

• Book ID: 102892901
• Publisher: Journal of Heterocyclic Chemistry
• Year: 1999
• Tongue: English
• Weight: 519 KB
• Volume: 36
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570360209

✦ Synopsis

Abstract

Allyloxy‐substituted macrocyclic dibenzodicyclohexanotetraamide 2 was prepared by the following sequence. MonoBoc‐protected chiral 1,2‐cyclohexanediamine (3) was treated with isophthaloyl chloride followed by removal of the Boc group to form bisisophthalamide 5. Compound 5 was then treated with allyloxyphthaloyl chloride to form the macrocyclic tetraamide 2 in a 56% yield. Chiral selector 2 was converted to its ethoxydimethylsilane derivative and heated in a suspension of silica gel and toluene to form the chiral macrocycle‐containing silica gel phase 1. This phase separated the enantiomers of (±)‐α‐methylbenzylamine and (±)‐DL‐α‐aminobutyric acid methyl ester in a liquid chromatograph.