2-Methyl-2-butene → HCID 178439230, compound

Participants

Reaction Steps

To a suspension (partially dissolved) of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[trans-4-(2-oxoethyl)cyclohexyl]methyl}benzamide (50 mg, 0.113 mmol, EXAMPLE 43, Step B) in t-butanol (4 ml) was added 2-methyl-2-butene (0.060 ml, 0.570 mmol), and then a solution of sodium chlorite (25 mg, 0.276 mmol) and sodium dihydrogen phosphate (27 mg, 0.225 mmol) in water (1 ml). The mixture was stirred overnight at room temperature (the mixture remained a finely divided suspension), at which point LC/MS analysis showed no starting material. The mixture was diluted with 10 ml of water and 10 ml of ethyl acetate. The phases were separated and the aqueous phase was acidified to pH 4 and extracted with 2×10 ml of ethyl acetate. The combined organics were washed with 10 ml of brine, dried (sodium sulfate), and concentrated to provide the title compound (52 mg, 0.113 mmol, 100% yield). Mass spectrum (ESI) 459.8 (M+1).

Provenance & Evidence