Water → HCID 18442426, compound

Participants

Reaction Conditions

Reaction Steps

To 3,3-dibutyl-4-oxo-5-(4-nitrophenyl)-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 103; 2.57 g, 5.8 mmol) was added DCM (130 ml), water (130 ml) and K2CO3 (2.44 g, 17.6 mmol). The reaction mixture was cooled down to 0° C. and m-chloroperoxybenzoic acid (3.42 g, 13.9 mmol) was added in one portion. The reaction was allowed to complete overnight with the temperature slowly rising to room temperature. Then NaHCO3aq (sat) was added and the two layers were separated. The water layer was then extracted three times with DCM. The combined organic layers was dried, filtered and evaporated under reduced pressure. The product was purified by flash chromatography using DCM as eluent to give the title compound 2.4 g (87%). M/z 475.4.

Provenance & Evidence