Hydrochloric Acid → HCID 5271821, compound

Participants

Reaction Steps

In 2.0 mL of methanol was dissolved 0.15 g of [(2R,3R,4R,5R)-5-[3-(aminocarbonyl)-5-fluoro-2-oxo-1(2H)-pyrazinyl]-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate. Then, 0.14 g of a 28% methanolic solution of sodium methoxide was added and stirred at an ice-cooled temperature for 20 minutes and thereafter at room temperature for 30 minutes. The reaction mixture was acidified with 0.75 mL of 1 mol/L hydrochloric acid and the solvent was removed under reduced pressure. After purifying the residue by column chromatography [eluent: chloroform:methanol=5:1], isopropanol and diethyl ether were added and the solid product was collected by filtration to obtain 40 mg of 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxamide.

Provenance & Evidence