Sodium Acetate → Thymidine acetate

HRID 1781574Notes

Reaction equation

HRID 1781574 reaction equation
Br[C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][C:10](=[O:12])[CH3:11])[O:4][C@H:3]1[N:13]1[CH:20]=[C:19]([CH3:21])[C:17](=[O:18])[NH:16][C:14]1=[O:15].C([O-])(=O)C.[Na+].[H][H]>CO.S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O>[C:10]([O:9][CH2:8][C@H:5]1[O:4][C@@H:3]([N:13]2[CH:20]=[C:19]([CH3:21])[C:17](=[O:18])[NH:16][C:14]2=[O:15])[CH2:2][C@@H:6]1[OH:7])(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 22873065HCID 22873065, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9814370Thymidine acetateYield 38.1%

Reagents, catalysts & solvents 2

HCID 17887766Palladium barium sulphateCatalystHCID 887MethanolSolvent

Procedure

12.47 g (28.1 mmol) of 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine were dissolved in 240 ml of methanol, and 6.91 g (3 equivalents) of sodium acetate were added thereto. To the reaction mixture, were added 1.25 g of 5% palladium-barium sulfate catalyst (0.1 equivalent). Then, the reaction system was filled with hydrogen gas and reacted for 24 hours at room temperature. The catalyst was removed from the reaction mixture, 100 ml of water were added, and the reaction mixture was neutralized to have a pH of 7.0 by adding an aqueous 25% sodium hydroxide solution thereto. The resulting solution was concentrated to about 100 ml, sodium chloride was added thereto until saturation, and the thus-saturated solution was extracted with ethyl acetate. The thus-extracted organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain white crystals. The crystals were washed with a small amount of methylene chloride to obtain 3.04 g (10.7 mmol) of 5'-O-acetylthymidine. Its yield was 38.1%.

Workup

  1. customreacted for 24 hours at room temperature
  2. customThe catalyst was removed from the reaction mixture, 100 ml of water
  3. additionwere added
  4. additionby adding an aqueous 25% sodium hydroxide solution
  5. concentrationThe resulting solution was concentrated to about 100 ml, sodium chloride
  6. additionwas added
  7. extractionuntil saturation, and the thus-saturated solution was extracted with ethyl acetate
  8. washThe thus-extracted organic layer was washed with saturated saline solution
  9. dry with materialdried with anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto obtain white crystals
  12. washThe crystals were washed with a small amount of methylene chloride

Sources & evidence

ORD record
ord-3257e360c2f74fb392e93d05e85ea09c
Source dataset
uspto-grants-1997_05
Patent number
US05633366

Reaction notes

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