Simultaneous chiral resolution of two racemic compounds by preferential cocrystallization

Fuli Zhou, Oleksii Shemchuk, Maxime D. Charpentier, Chloé Matheys, Laurent Collard, Joop H. ter Horst, Tom Leyssens

Research output: Contribution to journalArticlepeer-review

Abstract

We tap into an unexplored area of preferential crystallization, being the first to develop simultaneous chiral resolution of two racemic compounds by preferential cocrystallization. We highlight how the two racemic compounds RS-mandelic acid (MAN) and RS-etiracetam (ETI) can be combined together as enantiospecific R-MAN⋅R-ETI and S-MAN⋅S-ETI cocrystals forming a stable conglomerate system and subsequently develop a cyclic preferential crystallization allowing to simultaneous resolve both compounds. The developed process leads to excellent enantiopurity both for etiracetam (ee>98 %) and mandelic acid (ee≈95 %) enantiomers.

Original languageEnglish
Pages (from-to)20264-20268
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number37
Early online date6 Aug 2021
DOIs
Publication statusPublished - 6 Sep 2021

Keywords

  • chiral resolution
  • cocrystals
  • conglomerate
  • preferential crystallization
  • simultaneous resolution

Fingerprint

Dive into the research topics of 'Simultaneous chiral resolution of two racemic compounds by preferential cocrystallization'. Together they form a unique fingerprint.

Cite this