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

Autor: Kejiang Hu, Naijun Wu, N. Kent Dalley, Krzysztof E. Krakowiak, Jerald S. Bradshaw, Milton L. Lee
Rok vydání: 1999
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 36:381-387
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570360209
Popis: 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.
Databáze: OpenAIRE
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