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N-[(2S)-4-Chloro-2-(l-menth-yloxy)-5-oxo-2,5-dihydro-furan-3-yl]-l-valine.

ABSTRACT: The title compound, C(19)H(30)ClNO(5), was obtained by the tandem asymmetric Michael addition-elimination reaction of (5S)-3,4-dichloro-5-(l-menth-yloxy)furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The furan-one unit is approximately planar (r.m.s. deviation = 0.0204?Å) and the six-membered cyclo-hexane ring adopts a chair conformation. The crystal structure is stabilized by a network of O-H?O and N-H?O hydrogen bonds.

SUBMITTER: Song XM 

PROVIDER: S-EPMC2969247 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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N-[(2S)-4-Chloro-2-(l-menth-yloxy)-5-oxo-2,5-dihydro-furan-3-yl]-l-valine.

Song Xiu-Mei XM   Li Zhao-Yang ZY   Wang Zhao-Yang ZY   Li Jian-Xiao JX  

Acta crystallographica. Section E, Structure reports online 20090617 Pt 7

The title compound, C(19)H(30)ClNO(5), was obtained by the tandem asymmetric Michael addition-elimination reaction of (5S)-3,4-dichloro-5-(l-menth-yloxy)furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The furan-one unit is approximately planar (r.m.s. deviation = 0.0204 Å) and the six-membered cyclo-hexane ring adopts a chair conformation. The crystal structure is stabilized by a network of O-H⋯O and N-H⋯O hydrogen bonds. ...[more]

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