Direct High-Performance Liquid Chromatographic Resolution Of 2-Aryl And 2-Heteroarylpropionic Acids On A Chiral Stationary Phase Containing The N,N'-Dinitrobenzoyl Derivative Of (1R,2R)-Diaminocyclohexane

Racemic mixtures of eight non steroidal anti-inflammatory agents (derivatives of arylpropionic acids) were separated as 1-naphthalenemethylamides by HPLC on a chiral stationary phase containing the N,N'-3,5-dinitrobenzoyl derivative of (1R,2R)-diaminocyclohexane as chiral selector. Ibuprofen N,N-diethylamide, n-hexylamide and benzylamide and naproxen n-hexylamide and benzylamide were also resolved with chromatographic separation factors comparable to those obtained for the corresponding 1-naphthalenemethylamides; however, the latter derivatives showed significantly greater capacity factors (k'). The α values ranged from 1.10 to 1.83 and the k' values from 1.88 to 18.40 on a 250 x 4.0 mm I.D. stainless-steel column using n-hexane-2-propanol as the mobile phase.