Ethyl Acetate → N-(2-((tert-butyl(dimethyl)silyl)oxy)ethyl)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

Participants

Reaction Steps

N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide (0.400 g, 1.10 mmol) was combined with cesium carbonate (0.538 g, 1.65 mmol) in DMF (5 mL). The slurry was stirred at rt for 30 min, then to it was added (2-bromoethoxy)(tert-butyl)dimethylsilane (0.527 g, 2.20 mmol). The resulting mixture was stirred at rt for 18 h. Dilution with ethyl acetate (60 mL) and water (40 mL) followed by shaking gave a separation of phases. The organic phase was isolated, washed with water (2×30 mL) and brine (25 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to a residue. Purification by silica gel chromatography (gradient 100% DCM to 100:1 DCM:MeOH) gave the title compound as a yellow solid (0.560 g, 98% yield). LCMS: m/z 522 (M+H+), retention time 2.22 min (method 11). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 0.01 (s, 6H) 0.86 (s, 9H) 2.75 (t, J=5.95 Hz, 2H) 3.05 (s, 8H) 3.44 (t, J=5.49 Hz, 2H) 3.57 (t, J=6.41 Hz, 2H) 3.70 (t, J=5.49 Hz, 2H) 7.63-7.78 (m, 3H) 8.02-8.11 (m, 1H).

Provenance & Evidence