Hydrochloric Acid → Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate

Participants

Reaction Steps

2-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-4-carboxylic acid, (0.060 g, 0.14 mmol) in dimethyl formamide (10 mL) was added HOBT (0.025 g, 0.165 mmol), EDCI (0.035 g, 0.18 mmol), DIPEA (0.058 g, 0.45 mmol) and ammonium chloride (0.008 g, 0.15 mmol). The reaction mixture was stirred at room temperature for 20 hr, cooled and poured into water (10 mL). The pH was adjusted to 3 with 1N aqueous hydrochloric acid. The solution was extracted with dichloromethane (70 mL×3). The solution was washed with brine, dried, condensed in vacuum and separated by silica gel chromatography (ethyl acetate:methanol=1:0 to 10:1) to afford benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate 0.045 g solid (yield: 75.2%); LC-MS (ESI) m/z 416 [M+1]+.

Provenance & Evidence