1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68115504, compound

Participants

Reaction Steps

To a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added a solution of 2-[[(3S)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methoxy]acetic acid (120 mg, 0.24 mmol, 1.00 equiv), HOBT (49 mg, 0.36 mmol, 1.49 equiv), EDCI (70 mg, 0.37 mmol, 1.50 equiv), 4-dimethylaminopyridine (44 mg, 0.36 mmol, 1.48 equiv) and NH4Cl (76 mg, 1.42 mmol, 5.82 equiv) in distilled DMF (5 mL) at room temperature under nitrogen. The resulting solution was stirred for 14 hrs at ambient temperature, quenched with water and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to afford the desired tert-butyl N-(4-[[(3S)-3-[(carbamoylmethoxy)methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (75 mg, 63%) as a colorless oil. MS: m/z 491 (M+H)+.

Provenance & Evidence