Imidazole → HCID 22866806, compound

HRID 263696Notes

Reaction equation

HRID 263696 reaction equation
[C:1]([C@:9]([C@@H:16]([CH:18]([C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:19])[OH:17])([OH:15])[C:10]([F:14])([F:13])[CH:11]=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].CN(C)C=[O:44]>>[Si:33]([O:12][C:11]([C:10]([F:13])([F:14])[C@@:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C@@H:16]([CH:18]([C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:19])[OH:17])[OH:15])=[O:44])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 86749968HCID 86749968, compound

Product 1

HCID 22866806HCID 22866806, compound

Procedure

To a solution of 22.1 g (58 mmol) of 3,5-bis(benzoyl)-2-deoxy-2,2-difluororibose and 8.0 g (116 mmol) of imidazole in 410 ml of dimethylformamide (DMF) was added 8.8 g (58 mmol) of t-butyldimethylsilyl chloride. This reaction mixture was stirred for 12 hours at ambient temperature. The mixture was evaporated to dryness under reduced pressure. The residue was mixed with ethyl acetate and washed with 1.0N hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution, dried with sodium sulfate and evaporated to dryness under reduced pressure to yield 24.5 g of 1-(t-butyldimethylsilyloxy)-3, 5-bis(benzoyl)-2-deoxy-2,2-difluororibose.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. additionThe residue was mixed with ethyl acetate
  3. washwashed with 1.0N hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2facba2fbcf6428faa0442e99fb192c3
Source dataset
uspto-grants-1997_07
Patent number
US05644043

Reaction notes

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