Abstract:

Chiral 2-arylcarboxylic acid derivatives are important intermediates for preparing 2-arylcarboxylic acids, which are non-steroidal anti-inflammatory drugs (NSAIDs). In order to separate 2-phenylcarboxylic acid ester enantiomers by capillary gas chromatography (CGC), 2,6-di-O-pentyl-3-O-butyryl- β-cyclodextrin and 2,6-di-O-benzyl-3-O-heptanoyl- β-cyclodextrin were used as CGC chiral stationary phases, separately, and their enantioseparation abilities to enantiomers of methyl 2-phenylbutanoate, ethyl 2-phenylbutanoate, isopropyl 2-phenylbutanoate, methyl 2-phenylpropionate and cyclopentyl 2-phenylpropionate were examined. It was found that methyl 2-phenylbutanoate, methyl 2-phenylpropionate and cyclopentyl 2-phenylpropionate were successfully separated by using 2,6-di-O-pentyl-3-O-butyryl- β-cyclodextrin and 2,6-di-O-benzyl-3-O-heptanoyl- β-cyclodextrin as CGC chiral stationary phases, respectively. The enantiomer separation abilities of 2,6-di-O-pentyl-3-O-butyryl- β-cyclodextrin to the three pairs of 2-phenylcarboxylic acid esters tested are superior to those of 2,6-di-O-benzyl-3-O-heptanoyl- β-cyclodextrin.

Key words: β-cyclodextrin derivatives, 2-phenylcarboxylic acid esters, capillary gas chromatography (CGC), chiral stationary phases, enantiomer separation