Water → HCID 18323823, compound

Participants

Reaction Steps

The sulfoxide of Example 37, (100 mg, 0.3 mmoles) was stirred in 4 mL of CH2Cl2 and 8 mL water with 20 mg (0.09 mmole) of benzyltriethylammonium chloride and 94.5 mg (0.6 mmole) KMnO4 at 25° C. for 16 h. The mixture was partitioned between 60 mL EtOAc and 40 mL water and the EtOAc was washed with water, brine, dried and stripped in vacuo. The residue was purified by silica gel chromatography using 25% EtOAc/hexanes to give 85 mg product (81% yield); mp 174-175.3° C. Elemental analysis for C18H25N3O2S: Theory C, 62.22; H, 7.25; N, 12.09; S, 9.23. Found: C, 62.13; H, 7.28; N, 11.93; S, 9.12.

Provenance & Evidence