Acetic Acid → HCID 60126645, compound

HRID 392323Notes

Reaction equation

HRID 392323 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[CH:8]([CH2:14][O:15][P:16]([O:22][CH2:23][CH:24]=[CH2:25])([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[O:7][C@H:6]1[N:26]1[CH:31]=[C:30]([F:32])[N:29]=[C:28]([C:33]([NH2:35])=[O:34])[C:27]1=[O:36])(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[P:16]([O:22][CH2:23][CH:24]=[CH2:25])([O:18][CH2:19][CH:20]=[CH2:21])([O:15][CH2:14][C@@H:8]1[C@@H:9]([OH:10])[C@@H:5]([OH:4])[C@H:6]([N:26]2[CH:31]=[C:30]([F:32])[N:29]=[C:28]([C:33]([NH2:35])=[O:34])[C:27]2=[O:36])[O:7]1)=[O:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 69921403HCID 69921403, compound

Product 1

HCID 60126645HCID 60126645, compoundYield 180.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customOn 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
  4. customBoth the reaction mixtures
  5. custompurified by silica gel column chromatography [eluent: chloroform:methanol=40:1]

Sources & evidence

ORD record
ord-a13d82c002424c35a90a59666df3dcc3
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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