The Resolution of Enantiomeric Ibuprofen on Chiral Stationary Phases Containing N‐Arylcarbamoyl Derivatives of Phenylglycine

Abstract

AbstractA series of fourteen anilide derivatives of ibuprofen were resolved on six chiral stationary phases (CSPs) derived from N‐arylcarbamoyl derivatives of (S)‐phenylglycine. Excellent chiral resolutions were achieved on these CSPs. The ionic‐type CSPs showed better chiral recognition abilities than the corresponding covalent‐type CSPs, and the CSP bearing two chiral centers has better performance than the CSPs bearing only one chiral center. The highest separation factor was achieved using the ionic‐type CSP bearing two chiral centers for the resolution of the 3,5‐dinitroanilide derivative of ibuprofen. This result is better than those reported in literature for the resolution of ibuprofen on the CSPs derived from amino acids, According to the chromatographic behaviors, the hydrogen bonding interaction, the π‐π interactions provided by the phenyl groups in CSPs bearing one chiral center, and the phenylethylcarbamoyl moiety in CSPs bearing two chiral centers dominate the chiral recognition.