RESOLUTION OF AMIDE DERIVATIVES OF NAPROXEN ON PIRKLE-TYPE PI-ACIDIC CHIRAL STATIONARY PHASES

A chiral recognition model which explains the chiral resolution behavior of N-alkyl amide derivatives of naproxen on the Pirkle type pi-acidic CSPs derived from N-(3,5-dinitrobenzoyl)-(R)-phenylglycine and N-(3,5-dinitrobenzoyl)-(S)-leucine has been proposed. Based on the proposed model, an effort to improve the resolution of racemic naproxen derivatives on the CSP has been devoted and consequently, N-alkyl N-aryl amides of naproxen or N-alkyl N-cyclohexyl amides of naproxen have been found to be resolved quite well on a Pirkle type pi-acidic CSP. Based on the reciprocity conception of chiral recognition, CSPs which might show excellent resolving ability for pi-acidic racemic compounds have been suggested.