Trimethylsilyl triflate → 2-Chloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985814Notes

Reaction equation

HRID 1985814 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.C(O[CH:27]1[O:39][C@H:38]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]1[O:29][C:30](=[O:32])[CH3:31])(=O)C.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:1][C:2]1[N:6]([C@@H:27]2[O:39][C@H:38]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]2[O:29][C:30](=[O:32])[CH3:31])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 785722-ChlorobenzimidazoleHCID 516892Sodium BicarbonateHCID 9797055D-Ribofuranose, 1,2,3,5-tetraacetate

Product 1

HCID 218173932-Chloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazoleYield 61.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-Chlorobenzimidazole (7.5 g) and N,O-bis(trimethylsilyl)acetoamide (18.3 mL) were suspended in acetonitrile (150 mL), and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was allowed to cool to room temperature. To the mixture was added trifluoromethanesulfonic acid trimethylsilyl ester (17.9 mL), and the mixture was stirred for 15 minutes. To the reaction mixture was added 1,2,3,5-tetra-O-acetyl-D-ribofuranose (17.3 g), and the mixture was stirred at room temperature for 6 hour. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/10) to give the title compound (12.4 g).

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture was stirred for 15 minutes
  3. stirringthe mixture was stirred at room temperature for 6 hour
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-1f04a00f90ca4549820aa50025314302
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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