Dimethyl Sulfoxide → HCID 15871736, compound

Participants

Reaction Steps

Dimethyl sulphoxide (1.61 g, 20.6 mmol) was added dropwise to a solution of oxalyl chloride (1.31 g, 10.3 mmol) in dichloromethane (75 ml) at -60° C. The mixture was stirred until gas evolution had ceased. Ethyl trans-7-chloro-5-(1-naphthyl)-1-(2,2-dimethyl-3-hydroxypropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (4.6 g, 9.4 mmol), dissolved in dichloromethane (30 ml), was added dropwise over a period of 5 min. at -60° C., and stirring was continued for further 15 min. The mixture was quenched with triethylamine (4.73 g, 46.8 mmol) before allowing to warm to room temperature. Addition of water, separation of the organic layer and repeated extraction of the aqueous layer with dichloromethane was followed by drying of the combined organic layers with MgSO4. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (dichloromethane/methanol 99:1) to give the title compound (4.62 g, 99%).

Provenance & Evidence