Tetrahydrofuran → Ethyl hexanoate

Participants

Reaction Steps

To a solution of 3-[5-Amino-3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]hexanoic acid: ethyl ester (50 mg, 0.111 mmol) in THF (30 ml) was added TMS isocynate (1.73 mg, 15 mmol). The solution was stirred at RT for 3 hours. The reaction was checked by LCMS. To the reaction mixture an aqeous solution of Sodium bicarbonate (60 ml) was added. The resulting mixture, stirred for another 30 minutes, was then extracted with Ethyl Acetate. The organic layer, dried over MgSO4, was filtered and evaporated to dryness to give a dark residue. The residue was purified by prep TLC, eluded with 10% methanol in Dichloromethane to give 10 mg (18%) of 3-[3-1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-5-ureido-2,3-dihydro-benzoimidazol-1-yl]hexanoic acid ethyl ester. LCMS (ESMS): m/z 491.58 (M+H).

Provenance & Evidence