2-Methoxyethyl chloroformate → HCID 58758461, 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 (0.5 ml), then cooled to 0° C. 2-Methoxyethyl chloroformate (0.2 ml, 1.73 mmol) was added, the mixture was stirred at 0° C. for 45 minutes followed by addition of a second portion of 2-methoxyethyl chloroformate. The mixture was stirred for one additional hour at 0° C., 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 product containing fractions and trituration of the resulting solid with diethyl ether yielded the title compound as a white solid (0.20 g), melting point: 112° C.

Provenance & Evidence