Sodium bis(trimethylsilyl)amide → 7-[[4-(1-(tert-Butyldimethylsilanyloxy)hexyl)benzyl]methanesulfonylamino]-heptanoic Acid Ethyl Ester

Participants

Reaction Steps

Sodium bis(trimethylsilyl)amide (1.0 mL of a 1.0 M solution in THF, 1.00 mmol) was added to a solution of the sulfonamide 4 (220 mg, 0.88 mmol) in THF (2.2 mL) at 0° C. The reaction was warmed to room temperature and a solution of the iodide 9 (432 mg, 1.00 mmol) in THF (3.0 mL) was added. The reaction was stirred at room temperature for 16 h, quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 4:1 hex/EtOAc) gave 159 mg (29%) of the silyl ether 10 as a light yellow viscous oil.

Provenance & Evidence