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Exploring the Crystal Landscape of Mandelamide and Chiral Resolution via Cocrystallization
Shan Huang1, Deirbhile Fitzgerald2, Samuel A Koledoye1
1School of Chemistry, Analytical and Biological Chemistry Research Facility, SSPC, the SFI Research Centre for Pharmaceuticals, University College Cork, Cork T12 K8AF, Ireland.
Abstract:
The crystal structures of (±)-mandelamide, S-mandelamide, and enantioenriched mandelamide (94 S : 6 R) were determined. Diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline were synthesized. The diastereomeric cocrystal pairs of S-mandelamide with S/R-mandelic acid form 1:1 cocrystals in each case, while the diastereomeric cocrystal pairs of S-mandelamide with proline have different stoichiometries. Preliminary investigation of this diastereomeric cocrystal system for chiral resolution shows promise.
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