Attrition Induced Deracemisation of 2‑Fluorophenylglycine

By search of a library of closely related structures, two conglomerate imines of the amide of 2-fluorophenylglycine have been discovered and unambiguously characterized. One conglomerate is formed on reaction with benzaldehyde and the other on reaction with 4-Br-benzaldehyde. The crystal structures...

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Bibliographic Details
Published in:Organic process research & development 2015-01, Vol.19 (1), p.302-308
Main Authors: Wilmink, Patrick, Rougeot, Céline, Wurst, Klaus, Sanselme, Morgane, van der Meijden, Maarten, Saletra, Wojciech, Coquerel, Gérard, Kellogg, Richard M
Format: Article
Language:English
Subjects:
Chemical Sciences
Cristallography
Material chemistry
Medicinal Chemistry
Organic chemistry
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Summary:By search of a library of closely related structures, two conglomerate imines of the amide of 2-fluorophenylglycine have been discovered and unambiguously characterized. One conglomerate is formed on reaction with benzaldehyde and the other on reaction with 4-Br-benzaldehyde. The crystal structures of both have been determined. Both deracemise on grinding of the crystals under conditions whereby racemisation in solution can occur. Deracemisation of the former compound is hampered both by hydrate formation and formation of a polymorph. In contrast the latter deracemises efficiently. Hydrolysis of the enantiomerically pure (R)-imine to enantiomerically pure (R)-2-fluorophenylglycine proceeds smoothly. Either the (R)- or the (S)-enantiomer of the imine can be produced at will by seeding.
ISSN:1083-6160
1520-586X
DOI:10.1021/op500352m