Acetic Acid → HCID 22881710, compound

HRID 636279Notes

Reaction equation

HRID 636279 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:10][CH2:11]C)(=O)C.C(O)(=O)C.[Si:17]([O:24][C@@H:25]1[C@@H:29]([CH:30](OC)[OH:31])[O:28][C@@:27](C)([N:34]2[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[CH2:26]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CO>[Si:17]([O:24][C@@H:25]1[C@@H:29]([CH:30]([CH2:7][O:10][CH3:11])[OH:31])[O:28][C@@H:27]([N:34]2[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[CH2:26]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 131722400HCID 131722400, compound

Product 1

HCID 22881710HCID 22881710, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3′-O-t-butyldimethylsilyl-5′-(R)-C,O-methylenethymidine (1.84 g, 5 mmol) and anhydrous potassium carbonate (1.38 g, 10 mmol) in methanol was stirred at room temperature for 90 h. Ethyl acetate (70 ml) was added and the mixture neutralized with acetic acid to pH 7. Solvents were evaporated and the residue was dissolved in methylene chloride (30 ml). Precipitates were filtered and the solution concentrated- The residue was purified by chromatography on silica (EtOAc-hexane, 1:1) to give 310 mg of intact starting material and 578 mg of 3′-O-t-butyldimethylsilyl-5′-C-methoxy-methylthymidine as a colorless solid.

Workup

  1. customSolvents were evaporated
  2. dissolutionthe residue was dissolved in methylene chloride (30 ml)
  3. customPrecipitates
  4. filtrationwere filtered
  5. customthe solution concentrated- The residue was purified by chromatography on silica (EtOAc-hexane, 1:1)
  6. customto give 310 mg

Sources & evidence

ORD record
ord-b51dd0009ce94c5b918bb5ccfc441728
Source dataset
uspto-grants-2001_02
Patent number
US06191266B1

Reaction notes

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