Imidazole → (R)-N-[5-[2-Iodo-1-[((1,1-dimethylethyl)dimethylsilyl)oxy]ethyl]-2-(phenylmethoxy)phenyl]methanesulfonamide

Participants

Reaction Steps

To a stirred DMF (65 mL) solution containing (R)-2-iodo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol (12.7 g, 28 mmol), imidazole (5.25 g, 77 mmol), and 4-dimethylaminopyridine (0.30 g, 2.46 mmol) was added t-butyldimethylsilyl chloride (5.0 mL, 29.8 mmol). After 15 hours, the completed reaction was diluted with EtOAc (200 mL) and heptane (70 mL). The organic phase was washed 1×100 mL H2O, 2×100 mL aq. sat. CuSO4, 1×100 mL H2O, 1×100 mL sat'd brine, and dried over Na2SO4. The filtrate was concentrated in vacuo to give 15.81 g of a tan solid which was dissolved in ~125 mL CH2Cl2 and diluted with 650 mL heptane. The mixture was concentrated in vacuo at 40° C. to 42° C. until solids were seen (~105 mL distillate were collected), cooled to ~15° C. and filtered. The collected solids were washed with heptane and dried in vacuo at 45° C. to give 11.1 g (70%) of the title compound.

Provenance & Evidence