Effect of the mobile phase on the retention behavior of optical isomers of the mandelic acid derivative methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate by chiral HPLC

✍ Scribed by Baochun Shen; Xiuzhu Xu; Juanjuan Chen; Xuejun Zhang; Beijia Xu

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 94 KB
• Volume: 18
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20304

✦ Synopsis

Abstract

Conditions for separation of enantiomers of a mandelic acid derivative, methyl 2‐phenyl‐2‐(tetrahydropyranyloxy) acetate (the analyte) were studied. Because of the presence of two chiral carbons, the analyte consists of four stereoisomers stable at ambient temperature. Chiral HPLC of the analyte resulted in four peaks, using an (S,S)‐Whelk‐O1 column with the mobile phase consisting of hexane and the t‐butyl methyl ether (TBME). It was found that TBME dramatically changed the retention of the isomers, though it produced the best enantioseparation on (S,S)‐Whelk‐O1. The amount of TBME in the mobile phase influenced the degree of retention shift; 5% (v/v) TBME gave a bigger shift than 8% (v/v) and 10% (v/v). 2‐Propanol did not produce the same results. The chiral separation was also tried on cellulose tris (3, 5‐dimethyl phenylcarbamate) (CDMPC), but only three peaks were seen, indicating some but not full enantiomer resolution. Chirality, 2006. © 2006 Wiley‐Liss, Inc.