Optical resolution and configuration of 2-(4-dimethylvinylphenyl)propionic acid.
Optical resolution of (+/-)-2-(4-dimethylvinylphenyl)propionic acid (I) was performed through fractional crystallization of its salts with (S)-(-)- and (R)-(+)-alpha-phenylethylamine. 2-(4-Dimethylvinylphenyl)propionic acid, in comparison to ibuprofen, has greater antiinflammatory, analgesic and antipyretic activities, as well as a higher therapeutic index. Absolute configuration was determined by comparison of the (S)-(-)-alpha-phenylethylamide 1H-N.M.R. spectra of the enantiomers of (I) and of the enantiomers of ibuprofen whose configuration was already known. Thus, the absolute configuration (S) was assigned to (+)-(I).
D002851:Chromatography, High Pressure Liquid; D007052:Ibuprofen / Q000031:analogs & derivatives* / Q000032:analysis / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism
C042011:2-(4-dimethylvinylphenyl)propionic acid; D007052:Ibuprofen