Approximately 80% of pharmaceutical compounds are chiral and marketed as single enantiomers. Often, medicinally inactive enantiomers of a racemic mixture cause harmful side effects. Resolution is a critical step in obtaining optically pure products. For these reasons, it is of critical importance that students fully understand the process of resolution and its implications in the fields of medicine and pharmaceutical industry. This experiment was formulated for use in first semester Organic Chemistry curriculum. The presented experiment has several advantages over most resolution experiments. Naproxen is a commercially relevant product sold as (+)-naproxen due to the undesired side effects of the (-)-enantiomer.  Another advantage of this experiment is its research-based experimental design. Students are given the chance to compare different resolving agents and conditions so as to deduce the optimal method themselves. Preliminary results show that when optimized, the experimental procedure yields optical purity levels comparible to commercial naproxen (>90 % ee).

Investigations into the resolution process: Resolving ([plusmn]) naproxen

241st National Meeting (2011)

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