Imidazole → (R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide

Participants

Reaction Steps

To a solution of (R)-2-iodo-1-[4-(phenylmethoxy)-3-[(methyl-sulfonyl)amino]phenyl]ethanol (938 mg, 2.1 mmol), imidazole (393 mg, 5.77 mmol) and 4-dimethylaminopyridine (22.5 mg, 0.184 mmol) in dimethylformamide (10 mL) is added triethylsilyl chloride (0.38 mL, 2.2 mmol) with stirring. One hour thereafter, the reaction is complete, and the reaction solution is diluted with EtOAc (150 mL) and heptane (15 mL). The organic phase is washed with water, a saturated aqueous copper sulfate solution and a saturated brine, and dried over magnesium sulfate. The filtrate is concentrated under reduced pressure to give a solid, which is dissolved in ethyl acetate. The mixture is diluted with heptane, and the precipitated crystals are collected by filtration. The collected solid is washed with heptane and dried in vacuo to give the desired (R)—N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide (926 mg, yield: 79%).

Provenance & Evidence