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Simultaneous Chiral Resolution of Two Racemic Compounds by Preferential Cocrystallization **
Author(s) -
Zhou Fuli,
Shemchuk Oleksii,
Charpentier Maxime D.,
Matheys Chloé,
Collard Laurent,
ter Horst Joop H.,
Leyssens Tom
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202107804
Subject(s) - mandelic acid , enantiomer , crystallization , chiral resolution , chemistry , resolution (logic) , stereochemistry , kinetic resolution , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , artificial intelligence , computer science
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.