Imidazole → HCID 22866806, compound

HRID 1899795Notes

Reaction equation

HRID 1899795 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-30aa7fd4ed464e5796b08268f2df013c
Source dataset
uspto-grants-1996_11
Patent number
US05574021

Reaction notes

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