The resolution of praziquanamine, a derivative of the anti-schistosomiasis drug Praziquantel, has an unusual change in enantioselectivity when using two different aryl esters of L-tartaric acid. Dibenzoyl-L-tartaric acid affords (R)-praziquanamine as the major enantiomer while di-p-anisoyl-L-tartaric acid affords (S)-praziquanamine as the major enantiomer. In this work, crystals of all four combinations of (R)- and (S)-praziquanamine with dibenzoyl-L-tartaric acid and di-p-anisoyl-L-tartaric acid were grown by slow evaporation with a mixture of isopropanol:water and analyzed by X-ray diffractometry. Preliminary results show tighter packing patterns and a higher propensity for forming crystals within the matched pair of enantiomers and resolving agents, with the mismatched pairs showing looser crystal packing. Intermolecular interactions leading to these tendencies will be presented.

Crystal structure analysis of the chirality switching of the diastereomeric salt resolution of (±)-praziquanamine with two aryl esters of L-tartaric acid

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.