Exploring the Crystal Landscape of Mandelamide and Chiral Resolution via Cocrystallization
2024

Exploring Mandelamide Crystals and Chiral Resolution

publication Evidence: moderate

Author Information

Author(s): Huang Shan, Fitzgerald Deirbhile, Koledoye Samuel A., Collins Stuart G., Maguire Anita R., Lawrence Simon E.

Primary Institution: University College Cork

Hypothesis

Can cocrystallization be used to achieve chiral resolution of mandelamide?

Conclusion

The study successfully synthesized and characterized diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline, demonstrating potential for chiral resolution.

Supporting Evidence

  • The crystal structures of (±)-mandelamide, S-mandelamide, and enantioenriched mandelamide were determined.
  • Diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline were synthesized.
  • Preliminary investigation of the diastereomeric cocrystal system for chiral resolution shows promise.

Takeaway

The researchers made new types of crystals using mandelamide and other compounds, which could help separate different forms of drugs that are mirror images of each other.

Methodology

The study involved synthesizing diastereomeric cocrystal pairs through liquid-assisted grinding and slow evaporation, followed by characterization using thermal analysis, X-ray techniques, and FT-IR spectroscopy.

Limitations

The study primarily focused on specific cocrystal systems and may not generalize to all chiral compounds.

Digital Object Identifier (DOI)

10.1021/acs.cgd.3c01513

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