Exploring the Crystal Landscape of Mandelamide and\nChiral Resolution via Cocrystallization

The crystal structures\nof (±)-mandelamide, <i>S</i>-mandelamide, and enantioenriched\nmandelamide (94 <i>S</i> : 6 <i>R</i>) were determined.\nDiastereomeric cocrystal\npairs of <i>S</i>-mandelamide with both enantiomers of mandelic\nacid and proline were synthesized. The diastereomeric cocrystal pairs\nof <i>S</i>-mandelamide with <i>S</i>/<i>R</i>-mandelic acid form 1:1 cocrystals in each case, while\nthe diastereomeric cocrystal pairs of <i>S</i>-mandelamide\nwith proline have different stoichiometries. Preliminary investigation\nof this diastereomeric cocrystal system for chiral resolution shows\npromise.