Dicyclohexylcarbodiimide → HCID 70000079, compound

Participants

Reaction Steps

A solution of 2,2-dimethyl-1,3-dioxolane-4(R)-carboxylic acid (162 mg, 1.1 mmol) in dichloromethane (20 ml) under nitrogen was cooled with stirring to 4°, and treated successively with dicyclohexylcarbodiimide (227 mg, 1.1 mmol) and 1-hydroxybenzotriazole (147 mg, 1.1 mmol), then stirred at the same temperature for 1 hour. N,N-Diisopropylethylamine (129 mg, 1 mmol) was added, followed by 3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (399 mg, 0.92 mmol). The mixture was stirred for 2 hours, allowing the temperature to rise to ambient. Solid was filtered off, and the organic solution washed with water (2×20 ml), dried over magnesium sulfate and evaporated to dryness. The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (82 mg).

Provenance & Evidence