Methyl chloroformate → HCID 58758412, compound

Participants

Reaction Conditions

Reaction Steps

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1, 0.2 g, 0.46 mmol) was dissolved in DMF (4 ml) and pyridine (1 ml), then cooled to 0° C. Methyl chloroformate (0.2 ml, 2.57 mmol) was added and the mixture was stirred for 45 minutes at 0° C. A further portion of methyl chloroformate was added (0.2 ml), and the mixture was stirred for a further 2 hours 15 minutes before addition of a third portion of methyl chloroformate (0.2 ml). The mixture was stirred for a further hour at 0° C. after the third chloroformate addition, then diluted with water, extracted twice with ethyl acetate and dried over sodium sulfate. The residue obtained upon filtration and evaporation was purified via chromatography (silica gel, 0 to 10% acetonitrile in ethyl acetate). Evaporation of the fractions containing product and trituration of the resulting solid with diethyl ether yielded the title compound as a white solid (0.125 g), melting point: 205° C.

Provenance & Evidence