m-Chloroperbenzoic acid → Tert-butyl 4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylcarbamate

Participants

Reaction Steps

To a solution of the sulfide of Example 20 (1.00 g, 2.35 mmol) in dichloromethane (12 mL) at 0° C. was added purified mCPBA (0.423 g, 2.45 mmol) in dichloromethane (5 mL). After 1 h the ice/water bath was remove and the reaction was run for 1 h more. TLC shows no starting material and one slower running product spot. Additional dichloromethane was added and the mixture was washed with dilute aqueous sodium dithionite (1×) followed by 50% aqueous sodium bicarbonate (2×). The organic phase was dried (Na2SO4), filtered and evaporated. The residue was taken up into a solution of dichloromethane and diethyl ether and passed through a 5 cm pad of silica gel. Thorough removal of solvent in vacuo afforded 0.928 g of the title compound as a white solid.

Provenance & Evidence