HCID 23521443, compound → HCID 60126693, compound

HRID 392319Notes

Reaction equation

HRID 392319 reaction equation
[P:1]([O:33]CC1C=CC=CC=1)([O:25]CC1C=CC=CC=1)([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9]C(C)(C)[O:11]2)[C@H:7]([N:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH2:23])=[O:22])[C:16]2=[O:24])[O:6]1)=[O:2]>FC(F)(F)C(O)=O>[P:1]([OH:33])([OH:25])([O:3][CH2:4][C@@H:5]1[C@@H:12]([OH:11])[C@@H:8]([OH:9])[C@H:7]([N:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH2:23])=[O:22])[C:16]2=[O:24])[O:6]1)=[O:2]

Participants

3

Reactant 1

HCID 23521443HCID 23521443, compound

Product 1

HCID 60126693HCID 60126693, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 3 mL of 90% aqueous solution of trifluoroacetic acid was dissolved 60 mg of {(3aR,4R,6R,6aR)-6-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl dibenzyl phosphate at an ice-cooled temperature. After stirring the solution thus obtained at the same temperature as above for 30 minutes and further at room temperature for 2 hours, the solvent was removed under reduced pressure. Diethyl ether was added to the residue thus obtained, and the solid product was collected by filtration and washed with methanol. Thus, 15 mg of {(2R,3S,4R,5R)-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl dihydrogen phosphate was obtained as a light red-colored solid product.

Workup

  1. temperaturecooled temperature
  2. customthus obtained at the same temperature as above for 30 minutes and further at room temperature for 2 hours
  3. customthe solvent was removed under reduced pressure
  4. additionDiethyl ether was added to the residue
  5. customthus obtained
  6. filtrationthe solid product was collected by filtration
  7. washwashed with methanol

Sources & evidence

ORD record
ord-f5c2ca91ce2f4fa89aa3c489930a329a
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

Loading…