Water → HCID 86663876, compound

Participants

Reaction Steps

To a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (2.15 g) in THF (45 ml) were added triethylamine (2.39 mL) and methanesulfonyl chloride (0.98 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue (244 mg) was dissolved in acetonitrile (5 mL), cesium carbonate (184 mg) and thioacetic acid (0.04 mL) were added, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (45 mg).

Provenance & Evidence