Potassium Carbonate → HCID 118060108, compound

Participants

Reaction Steps

Ethyl ({[(tert-butoxycarbonyl)amino]sulfonyl}amino)acetate (1.00 g, 4.0 mmol) was mixed with N,N-dimethylformamide (DMF, 6.0 mL) and stirred at room temperature. Sodium iodide (0.01 g, 0.1 mmol, 0.025 equiv.), potassium carbonate (2.40 g, 20 mmol, 5.0 equiv.) and para-methoxybenzyl chloride (2.64 mL, 19.5 mmol, 4.875 equiv.) were added to the mixture. This reaction was warmed to 80° C. and stirred at 80° C. for 2 h. LCMS indicated reaction completion. The reaction was cooled to room temperature and filtered through Celite. The Celite bed was washed with dichloromethane and the combined organic filtrates were concentrated. The concentrated residue was dissolved in dichloromethane (20 mL) and washed with sodium bicarbonate (5×12 mL) and brine. The organic layer was dried over sodium sulfate and concentrated. The residue was purified on silica gel (0-40% ethyl acetate/hexane gradient elution) to give the desired product (1.39 g, 80%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.22 (m, 2H), 7.14 (m, 2H), 6.88 (m, 4H), 4.64 (s, 2H), 4.33 (s, 2H), 4.03 (q, 2H, J=7.1 Hz), 3.92 (s, 2H), 3.72 (s, 3H), 3.71 (s, 3H), 1.39 (s, 9H), 1.14 (t, 3H, J=7.1 Hz).

Provenance & Evidence