Ethyl Glycolate → Ethyl [[[[5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridin-2-yl]carbonyl]amino]methoxy]acetate

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Reaction Steps

A solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(hydroxymethyl)-4-methylpyridine-2-carboxamide (421 mg, 0.935 mmol) obtained from Example 85, ethyl hydroxyacetate (106 μl, 1.12 mmol), p-toluenesulfonic acid monohydrate (18 mg, 0.094 mmol) in benzene (10 ml) was heated to reflux for 30 minutes. The reaction solution was returned to room temperature, and then was concentrated under reduced pressure. Saturated aqueous sodium hydrogencarbonate was added to the resulting concentration residue, and the mixture was extracted from ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to flash silica gel column chromatography, and the fraction obtained from an elution with 35% ethyl acetate/hexane was concentrated under reduced pressure, to obtain the title compound (175 mg, 0.326 mmol, 35%) as a white solid.

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