Thiophenol → 3-((tert-butyl(dimethyl)silyl)oxy)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-1-propanamine

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Reaction Steps

N-(3-((tert-butyl(dimethyl)silyl)oxy)propyl)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide (0.540 g, 1.01 mmol) and thiophenol (0.333 g, 3.02 mmol) were combined in dry acetonitrile (10 mL). Potassium carbonate (0.557 g, 4.03 mmol) was added and the mixture was stirred at rt for 18 h. The mixture was diluted with ethyl acetate and filtered to remove unwanted solids. The crude filtrate was concentrated in vacuo, redissolved in methanol, and loaded onto a strong cation exchange resin cartridge to capture the desired product. Undesired materials were eluted from the cartridge with methanol, and then the desired material was released from the resin by elution with 2M ammonia in methanol. Concentration in vacuo gave the title compound as a yellow oil (0.294 g, 83% yield). No further purification was performed and the mixture was carried forward to the next step. LCMS: m/z 351 (M+H+), 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.06 (s, 6H) 0.90 (s, 9H) 1.75 (quin, J=6.46 Hz, 2H) 2.69-2.72 (m, 2H) 2.72-2.80 (m, 4H) 3.00-3.11 (m, 8H) 3.70 (t, J=6.02 Hz, 2H).

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