Ammonia → 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-carbamoyl-5-methylnitrobenzene

Participants

Reaction Steps

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-carboxy-5-methylnitrobenzene (3.6 g) in dichloromethane (60 ml) were added isobutyl chloroformate (1.4 ml) and triethylamine (1.6 ml) in an ice bath and the mixture was stirred at the same temperature for 0.5 hours. To the reaction mixture was added 28% aqueous ammonia (0.7 ml) and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/methanol=19/1 as an eluant to give the desired compound (3.9 g, yield quantitative) as a yellow oil.

Provenance & Evidence