Imidazole → 5'-O-tert-Butyldiphenylsilyl-thymidine

HRID 1488548Notes

Reaction equation

HRID 1488548 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H:19]1([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[CH2:20]1.N1C=CN=C1.C(Cl)Cl>CN(C)C=O.CO>[CH3:15][C:14]([Si:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:25][CH2:24][C@H:23]1[O:26][C@@H:19]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:20][C@@H:21]1[OH:22])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 5789ThymidineHCID 6344DichloromethaneHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 118128465'-O-tert-Butyldiphenylsilyl-thymidineYield 62.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

1.43 ml (5.5 mmol) of t-butyldiphenylsilyl chloride were added to a solution of 1.21 g (5 mmol) of thymidine and 0.749 g (11 mmol) of imidazole in 10 ml of dimethylformamide under an atmosphere of argon, and the resulting mixture was stirred at room temperature for 140 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in 100 ml of methylene chloride. The solution was then washed 5 times, each time with 100 ml of water. The solution was then dried over anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through 100 g of silica gel (70-230 mesh) using a gradient elution method, with methylene chloride containing from 0.5 to 3% by volume of methanol as the eluent, to give 1.5 g (yield 62%) of the title compound.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. dissolutionthe resulting residue was dissolved in 100 ml of methylene chloride
  3. washThe solution was then washed 5 times
  4. dry with materialThe solution was then dried over anhydrous magnesium sulfate
  5. distillationafter which the solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography through 100 g of silica gel (70-230 mesh)
  7. washa gradient elution method

Sources & evidence

ORD record
ord-936f74c06c1a4425a76f208b500c45ff
Source dataset
uspto-grants-1997_10
Patent number
US05674856

Reaction notes

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