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N-{4-Bromo-2-[(S)-menth-yloxy]-5-oxo-2,5-dihydro-3-fur-yl}-l-valine.

ABSTRACT: The title compound, C(19)H(30)BrNO(5), was obtained via a tandem asymmetric Michael addition-elimination reaction of 3,4-dibromo-5-[(S)-l-menth-yloxy]furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The mol-ecular structure contains an approximately planar (r.m.s. deviation = 0.0204?Å) five-membered furan-one ring and a six-membered menth-yloxy ring adopting a chair conformation. The crystal packing is stabilized by inter-molecular O-H?O and N-H?O hydrogen bonding.

SUBMITTER: Song XM

PROVIDER: S-EPMC2977280 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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N-{4-Bromo-2-[(S)-menth-yloxy]-5-oxo-2,5-dihydro-3-fur-yl}-l-valine.

Song Xiu-Mei XM Li Zhao-Yang ZY Wang Zhao-Yang ZY Fu Jian-Hua JH

Acta crystallographica. Section E, Structure reports online 20090711 Pt 8

The title compound, C(19)H(30)BrNO(5), was obtained via a tandem asymmetric Michael addition-elimination reaction of 3,4-dibromo-5-[(S)-l-menth-yloxy]furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The mol-ecular structure contains an approximately planar (r.m.s. deviation = 0.0204 Å) five-membered furan-one ring and a six-membered menth-yloxy ring adopting a chair conformation. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonding. ...[more]

PMID: 21583539

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