m-Chloroperbenzoic acid → HCID 69853689, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-{2-Hydroxy-3-[2-methanesulfonylamino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-4-phenyl-butyl}-5-methoxy-cyclohexanecarboxylic acid tert-butylamide (80 mg, 0.117 mmol) in dichloromethane (3 ml) was cooled to −10° C. A solution of meta-chloroperbenzoic acid in dichloromethane (2 ml) was added and the mixture stirred at −10° C. for 30 minutes. The solution was then washed with 5% aqueous sodium hydrogen carbonate solution, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give, after purification by flash chromatography on silica gel (dichloromethane/methanol: 97/3 2-{2-Hydroxy-3-[2-methanesulfonylamino-3-(naphthalen-2-sulfinyl)-propionylamino]-4-phenyl-butyl}-5-methoxy-cyclohexanecarboxylic acid tert-butylamide (65 mg, 70%) as a white solid. Mass spectrum, 701 [M+H]+. The following compounds were prepared in a similar manner, by oxidation of the appropriate sulphide:

Provenance & Evidence