Sodium Hydroxide → HCID 70456300, compound

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Reaction Steps

A solution of 1 g of tert-butyl 3(R)-[1(S)-ethoxycarbonyl-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate obtained in Example 1 in 100 ml of methylene chloride is added 0.51 g of m-chloroperbenzoic acid. After stirring for 30 minutes, 0.15 g of m-chloroperbenzoic acid is added, and stirring is continued for further 30 minutes. Fifty ml of 1N aqueous sodium hydroxide is added to the mixture, and the methylene chloride layer is separated, washed with water and concentrated under reduced pressure to yield tert-butyl 3(R)-[1(S)-ethoxycarbonyl-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate 1-oxide as a mixture of two stereoisomers. Separation by silica gel column chromatography yields 0.3 g of one isomer and 0.5 g of another isomer. Both are obtained as colorless oil. Mass spectrum of each isomer shows the peak due to molecular ion at 514.

Provenance & Evidence