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

doi:10.1002/ange.202107804

journal article Aug 06, 2021

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

Angewandte Chemie Vol. 133 No. 37 pp. 20426-20430 · Wiley

View at Publisher Save 10.1002/ange.202107804

Abstract

AbstractWe 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.

Topics

No keywords indexed for this article. Browse by subject →

References

47

[1]

Separation of enantiomers: needs, challenges, perspectives

Norbert M Maier, Pilar Franco, Wolfgang Lindner

Journal of Chromatography A 10.1016/s0021-9673(00)00532-x

[2]

10.1016/j.chroma.2009.10.022

[3]

10.1039/b713350b

[4]

[5]

10.1002/9780470608661

[6]

10.1016/0140-6736(91)92382-c

[7]

[8]

10.1002/9781118075647

[9]

10.2174/156802611795165098

[10]

10.1021/cr00013a009

[11]

10.1021/cr9500038

[12]

10.1002/1521-3773(20020617)41:12<2008::aid-anie2008>3.0.co;2-4

[13]

10.1002/1521-3757(20020617)114:12<2108::aid-ange2108>3.0.co;2-z

[14]

10.1002/anie.201302823

[15]

10.1002/ange.201302823

[16]

Beesley T. E. (1999)

[17]

10.1021/ja00389a064

[18]

10.1201/9781420042603

[19]

[20]

Innovative Chiral Resolution Using Enantiospecific Co-Crystallization in Solution

Géraldine Springuel, Tom Leyssens

Crystal Growth & Design 10.1021/cg300307z

[21]

10.1021/acs.cgd.7b01431

[22]

[23]

10.1007/128_2006_077

[24]

10.1039/c001895c

[25]

[26]

10.1021/cg901483v

[27]

10.1007/978-3-540-46320-7

[28]

10.1021/acs.cgd.6b01034

[29]

10.1021/op100173r

[30]

[31]

10.1002/anie.202002464

[32]

10.1002/ange.202002464

[33]

10.1016/j.addr.2007.05.011

[34]

10.1111/j.2042-7158.2010.01133.x

[35]

10.1517/17425247.2013.747508

[36]

[37]

10.1002/ceat.202000040

[38]

10.1021/acs.cgd.0c01236

[39]

10.1021/acs.cgd.9b01725

[40]

10.1016/s0957-4166(01)00527-4

[41]

10.1039/b714226a

[42]

[43]

10.1021/acs.oprd.5b00141

[44]

10.1002/chir.20135

[45]

[46]

10.1016/j.cep.2009.10.016

[47]

10.1016/j.cep.2005.11.013

Metrics

8

Citations

47

References

Details

Published: Aug 06, 2021
Vol/Issue: 133(37)
Pages: 20426-20430
License: View

Authors

F

Fuli Zhou