Acetic Acid → HCID 60126645, compound

Participants

Reaction Steps

In 4.0 mL of methanol was dissolved 0.23 g of (2R,3R,4R,SR)-4-(acetyloxy)-2-[3-(aminocarbonyl)-5-fluoro-2-oxo-1(2H)-pyrazinyl]-5-({[bis(allyloxy)-phosphoryl]oxy}methyl)tetrahydro-3-furanyl acetate. While cooling the solution with ice, 0.17 g of 28% methanol solution of sodium methoxide was added, and stirred for 5 minutes. Then, 0.15 mL of acetic acid was added, and the solvent was removed under reduced pressure. On the other hand, 1.0 g of (2R,3R,4R,5R)-4-(acetyloxy)-2-[3-(aminocarbonyl)-5-fluoro-2-oxo1(2H)-pyrazinyl]-5-({[bis(allyloxy)phosphoryl]oxy}methyl)tetrahydro-3-furanyl acetate was reacted in the same manner as above. Both the reaction mixtures were united and purified by silica gel column chromatography [eluent: chloroform:methanol=40:1]. Thus, 0.35 g of {(2R,3S,4R,5R)-5-[3-(aminocarbonyl)-5-fluoro-2-oxo-1(2H)-pyrazinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl diallyl phosphate was obtained as a yellow-colored solid product.

Provenance & Evidence