Iodine → HCID 21969095, compound

HRID 1421210Notes

Reaction equation

HRID 1421210 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:9][C@@H:8]([CH2:10][OH:11])[O:7][C@H:6]1[N:12]1[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14])(=[O:3])[CH3:2].[N+]([O-])([O-])=O.[Ce+4].[NH4+].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[I:47]I>C(#N)C>[C:1]([O:4][C@@H:5]1[CH2:9][C@@H:8]([CH:10]([I:47])[OH:11])[O:7][C@H:6]1[N:12]1[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 180504Ceric ammonium nitrateHCID 21969096HCID 21969096, compound

Product 1

HCID 21969095HCID 21969095, compoundYield 155.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2'-O-acetyl-3'-deoxyuridine (2.47 g) in acetonitrile (150 ml), diammonium cerium (IV) nitrate (2.51 g) and iodine (1.39 g) were added and allowed to react at 80° C. for one hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, the obtained residue w s extracted with ethyl acetate, and the extract was washed with 5% aqueous solution of sodium bisulfite and saturated brine. The ethyl acetate layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated to afford 2'-O-acetyl-3'-deoxy-5'-iodouridine (3.37 g, yield: 93.1%).

Workup

  1. customto react at 80° C. for one hour
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionthe obtained residue w s extracted with ethyl acetate
  5. washthe extract was washed with 5% aqueous solution of sodium bisulfite and saturated brine
  6. dry with materialThe ethyl acetate layer was dried with anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dfc862bedc2a404a9f7cf63995e0227c
Source dataset
uspto-grants-2000_06
Patent number
US06074824

Reaction notes

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