Enantiomeric separation of an aryloxyphenoxypropanoic acid by CE and LC

A capillary electrophoresis (CE) and an high performance liquid chromatography (HPLC) chiral separation have been developed for an aryloxyphenoxypropanoic acid, 2-[4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid, a new antitumor agent. The racemic mixture is analyzed, without derivatization, as the free acids. The CE assay is based on inclusion complexation with hydroxypropyl-beta-cyclodextrin. HPLC separation is achieved with a CSP column with the glycopeptide, teicoplanin, as the chiral selector. Both methods give baseline resolution to the R-and S-isomers. The methods were validated for assay and for optical purity assessment of the R-isomer. For assay, the HPLC method is precise (RSD < 0.6%), accurate (error, 0.5%) and linear (r2 = 0.9998). It is able to precisely (RSD = 0.5%) and accurately (error, 0.9%) detect 0.3-6.0% of one isomer (S) in the other (R). The CE assay is much less precise and accurate than HPLC. It is a good alternative to separate and detect the enantiomers, however.