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Synthesis of a chiral macrocyclic dibenzodicyclohexanotetraamide‐containing stationary phase for liquid chromatography
Author(s) -
Hu Kejiang,
Bradshaw Jerald S.,
Dalley N. Kent,
Krakowiak Krzysztof E.,
Wu Naijun,
Lee Milton L.
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360209
Subject(s) - chemistry , silica gel , enantiomer , derivative (finance) , yield (engineering) , toluene , chiral column chromatography , chloride , column chromatography , phase (matter) , chromatography , high performance liquid chromatography , organic chemistry , materials science , financial economics , economics , metallurgy
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.