Imidazole → HCID 85051032, compound

HRID 2179912Notes

Reaction equation

HRID 2179912 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH3:9][N:10]([CH3:32])[CH:11]1[C:25]2=[CH:26][CH:22]([O:23][C:24]2=[O:27])[CH:21]2[CH:17]([O:18][C:19](=[O:29])[CH:20]2[CH3:28])[CH2:16][C:15]2([CH3:30])[CH:13]([O:14]2)[CH:12]1[OH:31].N1C=CN=C1.O>CN(C=O)C>[O:31]([CH:12]1[CH:11]([N:10]([CH3:9])[CH3:32])[C:25]2=[CH:26][CH:22]([O:23][C:24]2=[O:27])[CH:21]2[CH:17]([O:18][C:19](=[O:29])[CH:20]2[CH3:28])[CH2:16][C:15]2([CH3:30])[CH:13]1[O:14]2)[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 86592994HCID 86592994, compound

Product 1

HCID 85051032HCID 85051032, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Terbutyldimethylsilyl chloride (80 μmol, 12 mg) is added to a solution of the compound of Example 5 (80 μmol; 27 mg) and imidazole (160 μmol; 11 mg) in DMF (0.5 ml). The solution obtained is stirred for 20 hours then the reaction mass is poured into water. The aqueous phase is extracted twice with ethyl acetate, the organic phase is washed with water then with a solution of sodium chloride. The organic phase is dried over magnesium sulphate, filtered then evaporated. The residue is eluted on silica with a mixture of isopropyl acetate and dichloromethane (20/80). 20 mg of product is obtained in the form of a white powder.

Workup

  1. customThe solution obtained
  2. extractionThe aqueous phase is extracted twice with ethyl acetate
  3. washthe organic phase is washed with water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customthen evaporated
  7. washThe residue is eluted on silica with a mixture of isopropyl acetate and dichloromethane (20/80)

Sources & evidence

ORD record
ord-48e14922316344b3a384cf25794cfdfe
Source dataset
uspto-grants-2005_05
Patent number
US06887869B2

Reaction notes

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