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N-[(2S)-4-Chloro-2-(l-menthyloxy)-5-oxo-2,5-dihydro-3-furyl]-l-alanine.

ABSTRACT: The title compound, C(17)H(26)ClNO(5), was prepared via a tandem asymmetric Michael addition-elimination reaction of (5S)-3,4-dichloro-5-(l-menth-yloxy)furan-2(5H)--one and l-alanine in the presence of potassium hydroxide. The five-membered furan-one ring is approximately planar while the six-membered menth-yloxy ring adopts a chair conformation. The crystal packing is stabilized by inter-molecular O-H?O and N-H?O hydrogen bonds.

SUBMITTER: Li ZY

PROVIDER: S-EPMC2977713 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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N-[(2S)-4-Chloro-2-(l-menthyloxy)-5-oxo-2,5-dihydro-3-furyl]-l-alanine.

Li Zhao-Yang ZY Song Xiu-Mei XM Wang Zhao-Yang ZY Yang Kai K

Acta crystallographica. Section E, Structure reports online 20090410 Pt 5

The title compound, C(17)H(26)ClNO(5), was prepared via a tandem asymmetric Michael addition-elimination reaction of (5S)-3,4-dichloro-5-(l-menth-yloxy)furan-2(5H)--one and l-alanine in the presence of potassium hydroxide. The five-membered furan-one ring is approximately planar while the six-membered menth-yloxy ring adopts a chair conformation. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds. ...[more]

PMID: 21583849

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