Dicyclohexylcarbodiimide → HCID 178495118, compound

Participants

Reaction Conditions

Reaction Steps

(3S)-3-Isothiocyanato-1-methoxy-butane (24.68 g, 169.94 mmol) is added to a suspension of methyl 2-[4-(5-amino-6-hydroxy-2-pyridyl)-5-(2,4-difluorophenyl)-1H-imidazol-2-yl]-2-methyl-propanoate (55 g, 141.62 mmol) in ethanol (550 mL) at RT. The reaction mixture is stirred under reflux overnight and then cooled to 50° C. Dicyclohexylcarbodiimide (37.99 g, 184.10 mmol) is added to the mixture and the resulting suspension is stirred under reflux for 20 h. The reaction is allowed to reach RT and the solvent evaporated under reduced pressure. The residue is absorbed in silica gel and purified through a silica gel column (first using dichloromethane as an eluent to remove the most apolar impurities and then with dichloromethane/methanol 95:5 to elute the desired product) to afford the title compound (52 g, 74%) as a dark brown foam. LC-ES/MS m/z 500 (M+1).

Provenance & Evidence