Ethyl Acetate → HCID 21309182, compound

HRID 443008Notes

Reaction equation

HRID 443008 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH:14]=[CH:15]C(OCC)=O)[O:12][C@@H:11]([N:21]2[CH:29]=[C:27]([CH3:28])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30]([O:33][CH2:34][CH3:35])(=[O:32])[CH3:31]>[Pd]>[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:31][C:30]([O:33][CH2:34][CH3:35])=[O:32])[O:12][C@@H:11]([N:21]2[CH:29]=[C:27]([CH3:28])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 54026584HCID 54026584, compound

Product 1

HCID 21309182HCID 21309182, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of 3'-O-t-butyldimethylsilyl-5'-carbethoxymethylene-5'-deoxy-thymidine (4.24 g, 10 mmol) in ethyl acetate was added 200 mg of 10% Pd/C under nitrogen atmosphere. The nitrogen gas was removed by vacuum and hydrogen was introduced. This procedure was repeated twice, and stirring was continued under atmospheric pressure of hydrogen for 16 hours. The catalyst was filtered over a celite pad, and the solvent was removed in vacuo. The title compound was crystallized from hexane/ethyl acetate. The title compound was obtained in 95% yield.

Workup

  1. customThe nitrogen gas was removed by vacuum and hydrogen
  2. additionwas introduced
  3. filtrationThe catalyst was filtered over a celite pad
  4. customthe solvent was removed in vacuo
  5. customThe title compound was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-53bc7a5421864849b718671748804055
Source dataset
uspto-grants-1999_04
Patent number
US05892024

Reaction notes

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