1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86695172, compound

Participants

Reaction Steps

To a solution of 2-[(12S)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetic acid (148 mg, 0.32 mmol, 1.00 equiv) in 6 mL of distilled DMF was added NH4Cl (103 mg, 1.93 mmol, 6.00 equiv), EDCI (92 mg, 0.48 mmol, 1.50 equiv), 4-dimethylaminopyridine (58 mg, 0.47 mmol, 1.50 equiv) and HOBt (65 mg, 0.48 mmol, 1.50 equiv) successively and the resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and extracted with 3×50 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to give 80 mg (54%) of the desired tert-butyl N-(4-[[(12S)-12-(carbamoylmethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate as a white solid. MS: m/z 460 (M+H)+.

Provenance & Evidence