Dichloromethane → HCID 54356446, compound

Participants

Reaction Steps

To a stirred solution of the thiazepine prepared in Step 8 of Example 482 (243.7 mg) in 25% H2O/acetone (8 mL) is added 4-methylmorpholine N-oxide (201.5 mg) followed by a solution of osmium tetroxide in 2-methyl-2-propanol (2.5 wt %, 30 μL). The reaction mixture is stirred at room temperature for 18 h. The reaction mixture is treated with saturated sodium bisulfate (8 mL), then poured into CH2Cl2 (50 mL). The phases are separated. The aqueous phase is extracted with CH2Cl2 (2×25 mL). The combined organic phases are washed with brine (1×25 mL), dried (MgSO4), filtered and concentrated. The residue is purified on a Biotage 40 S column using 1% CH3OH in CH2Cl2 as the eluent to afford 216.1 mg (0.47 mmol, 83%) of the thiazepine S,S-dioxide as a white solid. mp 144-146° C.

Provenance & Evidence