tert-Butyldimethylsilyl chloride → HCID 69621287, compound

HRID 547995Notes

Reaction equation

HRID 547995 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][N:13]([C@@H:16]2[S:22][C@H:21]([CH:23]([C:25]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[OH:24])[C@@H:19]([OH:20])[C@H:17]2[OH:18])[C:12](=[O:48])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:49][C:50]([Si:53](Cl)([CH3:55])[CH3:54])([CH3:52])[CH3:51]>C1COCC1.C(OCC)(=O)C.[N+]([O-])([O-])=O.[Ag+]>[C:1]([NH:9][C:10]1[CH:15]=[CH:14][N:13]([C@@H:16]2[S:22][C@H:21]([CH:23]([C:25]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:34]3[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=3)[OH:24])[C@@H:19]([OH:20])[C@@:17]2([Si:53]([C:50]([CH3:52])([CH3:51])[CH3:49])([CH3:55])[CH3:54])[OH:18])[C:12](=[O:48])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 86598591HCID 86598591, compound

Product 1

HCID 69621287HCID 69621287, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 21 (200 mg, 0.3 mmol), silver nitrate (100 mg, 0.6 mmol), and TBDMS-Cl (70 mg, 0.45 mmol) were dissolved in dry THF and stirred at room temperature overnight. The reaction was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to give Compound 23 (100 mg) in 45% yield. The 3-protected analog (N-benzoyl-1-[5-(4,4′-dimethoxytrityl)-3-(t-butyldimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine) was also isolated as a minor product.

Workup

  1. washwashed with saturated sodium bicarbonate solution, water and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-84bc187851454a66a3c8fc8c5afa2231
Source dataset
uspto-grants-2011_05
Patent number
US07939677B2

Reaction notes

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