A reverse phase HPLC method for the separation of two stereo isomers of 2‐[4‐(methylsulfonyl)phenyl]‐3‐(3 (r) ‐oxocyclopentyl)propanoic acid

This study describes successful method development and separation of two stereo isomers of 2‐[4‐(methylsulfonyl)phenyl]‐3‐(3 (R) ‐oxocyclopentyl)propanoic acid by reverse phase high‐performance liquid chromatography. Baseline resolution was achieved on a J'sphere‐ODS‐H80 (150 mm × 4.6 mm, 4 μm) column using mobile phase consisting of 0.05% triflouroacetic acid in water‐acetonitrile (85:15, v/v) at a flow rate of 1.0 ml/min. The detection was carried out at 228 nm. The title compound, in turn, can be obtained by C‐alkylation of methyl 2‐[4‐(methylthio)phenyl]acetate with 2( S )‐iodomethyl‐8,8‐dimethyl‐6,10‐dioxaspiro[4.5]decane followed by consecutive hydrolysis and oxidation . The partially validated analytical method (system suitability, peak homogeneity, linearity, precision, robustness, and solution stability) has limit of detection and limit of quantification, 0.15 and 0.50 μg/ml respectively. Alternatively, the new method is being routinely utilized to monitor epimerization of α‐carbon of the propanoic acid in the title compound by crystallization‐induced dynamic resolution. Chirality, 2011. © 2010 Wiley‐Liss, Inc.