Dicyclohexylcarbodiimide → 3-(4-(4-(3-(1-Triphenylmethyl-4-imidazolyl)propanoyl)-piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one

Participants

Reaction Steps

3-(1-Triphenylmethyl-4-imidazolyl)propionic acid (420 mg, 1.1 mmol) was suspended in dichloromethane (10 ml) under nitrogen, and treated successively with dicyclohexylcarbodiimide (227 mg, 1.1 mmol) and 1-hydroxybenzotriazole (149 mg, 1.1 mmol), then stirred at ambient temperature for 30 minutes. To it was added a solution of 3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (435 mg, 1 mmol) and N,N-diisopropylethylamine (258 mg, 2 mmol) in dichloromethane (5 ml). The mixture was stirred for 18 hours at the same temperature, solid filtered off, and the organic phase purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 15% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (460 mg).

Provenance & Evidence