A common NSAID, ibuprofen, is marketed as a racemic mixture. It's optically active isomer however, is more commercially valuable particularly to the pharmaceutical industry. Within the past few years investigators have been able to separate the enantiomers by traditional crystallization techniques using L-lysine as a resolving agent. This process, though successful, is time consuming because it is dependent upon crystal formation. The use of supercritical fluids affords a potential means to quick and inexpensive resolution. We have developed a resolving agent suitable for a supercrititcal carbon dioxide medium. Through preliminary molecular modeling studies using a augmented form of Allinger's MM3 force field, this agent appears sufficiently selective for the enantiomers of ibuprofen on a theoretical basis. We have synthesized and characterized our resolving agent, which is a fluorinated L-lysine derivative. Our attempts and theoretical expectations of enantiomeri ibuprofen separations in supercritical carbon dioxide will be related to the effectiveness of chiral amino acid systems in non-traditional media.
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