Pyridine → HCID 22877781, compound

HRID 2393321Notes

Reaction equation

HRID 2393321 reaction equation
FC(F)(F)C(O)=O.[CH:8]([Si:11]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[O:12][C@@H:13]1[C@@H:17]([CH2:18][O:19]C(C2C=CC=CC=2)(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)[O:16][C@@H:15]([N:43]2[CH:51]=[C:49]([CH3:50])[C:47](=[O:48])[NH:46][C:44]2=[O:45])[CH2:14]1)([CH3:10])[CH3:9].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH:55]([Si:11]([CH:8]([CH3:10])[CH3:9])([CH:52]([CH3:54])[CH3:53])[O:12][C@@H:13]1[C@@H:17]([CH2:18][OH:19])[O:16][C@@H:15]([N:43]2[CH:51]=[C:49]([CH3:50])[C:47](=[O:48])[NH:46][C:44]2=[O:45])[CH2:14]1)([CH3:56])[CH3:57]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 22877779HCID 22877779, compound

Product 1

HCID 22877781HCID 22877781, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.6 ml of trifluoroacetic acid were added dropwise to a solution of 1.861 g (2.655 mmol) of 3'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)thymidine [prepared as described in step (a) above] in 80 ml of chloroform, whilst cooling in an ice bath and stirring. The resulting mixture was stirred for 10 minutes and then 2 ml of pyridine were added. The reaction mixture was washed twice, each time with 100 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel (70-230 mesh), using methylene chloride containing 4% by volume of methanol as the eluent, to give 0.9965 g (yield 94%) of the title compound.

Workup

  1. temperaturewhilst cooling in an ice bath
  2. stirringThe resulting mixture was stirred for 10 minutes
  3. washThe reaction mixture was washed twice
  4. dry with materialeach time with 100 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through 50 g of silica gel (70-230 mesh)

Sources & evidence

ORD record
ord-a999ab228bab49b4b2436c26deb26d33
Source dataset
uspto-grants-1998_09
Patent number
US05807837

Reaction notes

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