N,N'-Dimethylethylenediamine → (R)-4-[4-(4-benzoyloxymethyl-2-oxooxazolidin-3-yl)-3-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

To a mixture of 4-(4-bromo-3-fluorobenzoyl)piperazine-1-carboxylic acid tert-butyl ester (3.49 g) described in Preparation Example 90, benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (1.99 g), potassium carbonate (2.49 g) and copper (I) iodide (343 mg) were added toluene (18 mL) and N,N′-dimethylethylenediamine (387 μL), and the mixture was refluxed for 3 hr. Since the starting materials were left, copper (I) iodide (343 mg) and N,N′-dimethylethylenediamine (387 μL) were added and the mixture was further refluxed for 4 hr. The reaction mixture was cooled, ethyl acetate and aqueous ammonium chloride solution were added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a 1:1 mixture of saturated aqueous ammonium chloride solution and ammonia water, and the mixture was washed once with saturated aqueous ammonium chloride solution, once with saturated aqueous sodium chloride solution, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (1.48 g).

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