Imidazole → HCID 22942422, compound

HRID 362690Notes

Reaction equation

HRID 362690 reaction equation
[C:1]([S:9][C@@H:10]1[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[O:12][C@H:11]1[N:18]1[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]1=[O:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>N1C=CC=CC=1>[Si:31]([O:17][CH2:16][C@H:13]1[O:12][C@@H:11]([N:18]2[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@H:10]([S:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@@H:14]1[OH:15])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 53760363HCID 53760363, compound

Product 1

HCID 22942422HCID 22942422, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

2'-Deoxy-2'-(benzoylthio)uridine (2.75 mmole) was dried by co-evaporation with dry pyridine (2×20 ml) and dissolved in dry pyridine (50 ml) containing imidazole (5 mmole); tert-butyldimethylsilyl chloride (5 mmole) was added with stirring. The reaction mixture was stirred at room temperature for 16 hr. Solvent was removed under vacuo and the residue was dissolved in CH2Cl2 (100 ml), washed with 5% sodium bicarbonate solution (2×50 ml) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-(benzoylthio) uridine which was purified on silica gel column chromatography.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hr
  2. customSolvent was removed under vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2 (100 ml)
  4. washwashed with 5% sodium bicarbonate solution (2×50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-d0ec15fb588740e780086d0646309fdb
Source dataset
uspto-grants-1999_02
Patent number
US05869696

Reaction notes

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