光学活性なカルボン酸のアミドを固定相とするガスクロマトグラフィーによる光学異性体の分離

概要

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Amide derivatives of three optically active carboxylic acids, N-(S)-2- (4-chlorophenyl)isovaleroyl laurylamine [I], W-(1R,3R)-trans-chrysanthemoyl laurylamine[II] and N-(1R,3S)-cis-chrysanthemoyl laurylamine[III] were synthesized and their properties as stationary phases for the separation of chiral compounds by gas chromatography were examined. These phases showed enantioselectivity for some enantiomers of N-trifluoroacetyl (TFA) amino acid esters, N-TFA-amines and carboxylic acid amides. Rather high separation factors were obtained for some carboxylic acid amide enantiomers. For example, racemic 2-ethyl-3,3-dimethylbutyric acid t-butylamide was separated (α=1.037, 100℃) with [I] and racemic trans-chrysanthemic acid t-butylamide was separated (α=1.074, 100℃) with [II], respectively. It was noticeable that these two carboxylic acid amides were hardly separated with N,N' ,N"-[2,4,6-(1,3,5-triazine) triyl]-tris-(L-valine isopropylester), N,N'-[2,4-(6-ethoxy-1,3,5-triazine)diyl]-bis-(L-valyl-L-valine isopropylester), N-lauroyl-L-valine t-butylamide and N-lauroyl-(R)-1-(α-naphthyl)ethylamine, which were proved to be excellent chiral phases for the separation of amino acid and amine enantiomers. In conclusion these optically active carboxylic acid amides are specifically effective as the stationary phase for the separation of some chiral carboxylic acid amides.
社団法人日本分析化学会の論文
1981-08-05