Ethyl Acetate → HCID 135681558, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of sodium hydride (60% in oil, 0.014 g, 0.352 mmol)in toluene (5 mL) was added [2-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-acetylamino]-acetic acid ethyl ester (0.135 g, 0.293 mmol) in tetrahydrofuran (5 mL) over 5 minutes. The mixture was stirred at 90–100° C. for 2.5 hours, then cooled down to ˜0° C. and ethyl acetate followed by aqueous ammonium chloride (˜3 mL) were added. The aqueous phase was extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was quickly purified by silica gel chromatography to give the title material (0.072 g, 59%) as a white solid. LCMS (+ESI, M+H+) m/z 415, (− ESI, M−H−) m/z 413; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 1.47 (9H, s), 3.06 (4H, br s), 3.74 (4H, br s), 3.94 (2H, br s), 6.83 (1H, s), 6.97 (1H, s), 12.1 (1H, m), 12.56 (1H, s).

Provenance & Evidence