2-Furancarboxylic acid → N-[(5S)-3-(3-Fluoro-4-(4-(2-Furoyloxymethyl)imidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

Participants

Reaction Steps

N-[(5S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide (174 mg, 0.5 mM) and furan-2-carboxylic acid (168 mg, 1.5 mM) were suspended in dry dichloromethane (20 ml) under argon, and N,N-dimethylformamide dineopentyl acetal (462 mg, 2 mM) added. The mixture was stirred at ambient temperature for 48 hours giving a solution. The mixture was diluted with an equal volume of dichworomethane, and washed with sufficent 5% aqueous sodium bicarbonate to remove all acids. The organic phase was dried over magnesium sulfate, evaporated, and the residue dissolved in dichloromethane and chromatographed on a 5 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the title product (184 mg).

Provenance & Evidence