Synthesis and X‐ray crystal structure study of the hydroxyurea and hydantoin derivatives of l‐valine
- 1 August 2005
- journal article
- research article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 66 (2), 85-93
- https://doi.org/10.1111/j.1399-3011.2005.00276.x
Abstract
The novel hydroxyurea 5 derivative of L-valine was prepared by aminolysis of N-(1-benzotriazolecarbonyl)-L-valine cyclohexanemethylamide 4 with hydroxylamine. The corresponding hydantoin derivative 6 was synthesized by base catalyzed cyclization of the amide 4. The exact stereostructure of hydantoin derivative 6 has been determined by X-ray crystal structure analysis. The chiral atom of the hydantoin ring in 6 has S configuration what is in agreement with its configuration in the starting L-valine. The molecules of 6 are joined into infinite chains by N-H center dot center dot center dot O intermolecular hydrogen bond. The infinite chains are additionally linked by two C-H center dot center dot center dot O hydrogen bonds, thus forming two-dimensional network. The hydantoin derivative of L-valine 6 and its L-leucine analogue LH have similar packing arrangements, so they are homostructural.Keywords
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