Imidazole → HCID 53726250, compound

HRID 1004619Notes

Reaction equation

HRID 1004619 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][C@H:15]([C@H:18]1[C@@H:21]([C:22]#[CH:23])[N:20]([C@@H:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:25])[C:19]1=[O:32])[CH2:16][CH3:17]>CN(C)C=O.C(OCC)(=O)C>[Si:6]([O:14][C@H:15]([C@H:18]1[C@@H:21]([C:22]#[CH:23])[N:20]([C@@H:24]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH3:25])[C:19]1=[O:32])[CH2:16][CH3:17])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 54511093HCID 54511093, compound

Product 1

HCID 53726250HCID 53726250, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (554 mg, 8.14 mmol) and tert-butyldimethylsilyl chloride (1.13 g, 7.52 mmol) were added to a solution of the compound (1.61 g, 6.26 mmol) prepared in Example 3 in N,N-dimethylformamide (7 ml) at room temperature in an argon atmosphere. After stirring overnight at this temperature, the mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of potassium hydrogensulfate and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=20/1) to obtain 2.157 g (yield 93%) of the title compound as a colorless oily substance.

Workup

  1. washThe organic layer was washed with saturated aqueous solution of potassium hydrogensulfate and saturated brine in this order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed by evaporation under reduced pressure
  4. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-75c7ee2f0ad947ae99338588dcd4e894
Source dataset
uspto-grants-2000_04
Patent number
US06051569

Reaction notes

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