Sodium Carbonate → HCID 15476622, compound

HRID 1033289Notes

Reaction equation

HRID 1033289 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[C@@H:7]1Br)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.[Pd]>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 12081666HCID 12081666, compound

Product 1

HCID 15476622HCID 15476622, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

After 5 g of 5'-O-acetyl-3'-deoxy-3'-bromoadenosine (X) was dissolved in 100 ml of acetonitrile, 1.71 g of sodium carbonate (dissolved in 10 ml of water) and 1.5 g of Pd/C were added to the solution. The mixture was stirred at room temperature for 2 hours under hydrogen atmosphere of 3.5 atms. The reaction solution was filtered and the residue was washed with ethyl acetate. The filtrate was combined with the washing liquid. After the organic solvent was distilled off under reduced pressure, the formed crystals were taken out by filtration. The crystals were dissolved in 200 ml of ethyl acetate. The solution was dried over magnesium sulfate and the drying agent was removed. The system was concentrated to give 2.7 g (yield, 69%) of 3'-deoxy-5'-O-acetyladenosine (XII).

Workup

  1. filtrationThe reaction solution was filtered
  2. washthe residue was washed with ethyl acetate
  3. distillationAfter the organic solvent was distilled off under reduced pressure
  4. filtrationthe formed crystals were taken out by filtration
  5. dissolutionThe crystals were dissolved in 200 ml of ethyl acetate
  6. dry with materialThe solution was dried over magnesium sulfate
  7. customthe drying agent was removed
  8. concentrationThe system was concentrated

Sources & evidence

ORD record
ord-3e3448c1285d433aa1623a7b649043e6
Source dataset
uspto-grants-1994_05
Patent number
US05310895

Reaction notes

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