Acetyl chloride → HCID 178475917, compound

HRID 1857732Notes

Reaction equation

HRID 1857732 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[C:13]([CH2:15][OH:16])[N:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:32]([O:16][CH2:15][C:13]1[N:14]=[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[NH:11][C:12]=1[S:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178455183HCID 178455183, compound

Product 1

HCID 178475917HCID 178475917, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 700 mg (1.8 mmol) of [2-t-butyldimethylsilyloxymethyl-5-(3-chlorophenylthio)-1H-imidazol-4-yl]methanol (46) in methylene chloride (14 ml), was added 1.29 g (12.8 mmol) of triethylamine, and then, 1.00 g (12.8 mmol) of acetyl chloride was added dropwise under ice-cooling with stirring. The reaction mixture was stirred at room temperature for 15 minutes, and added to a cooled saturated aqueous sodium hydrogen carbonate solution to neutralize and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure. The residue was dissolved in 5 ml of methanol, to which was added 5 ml of 50% aqueous acetic acid, and the mixture was stirred at room temperature for1 hour. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution to neutralize, and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:2) to give 602 mg of [2-t-butyldimethylsilyloxymethyl-5-(3-chlorophenylthio)-1H-imidazol-4-yl]methyl acetate as oil (yield 78%).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 15 minutes
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in 5 ml of methanol, to which
  8. additionwas added 5 ml of 50% aqueous acetic acid
  9. stirringthe mixture was stirred at room temperature for1 hour
  10. additionTo the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution
  11. extractionextracted with methylene chloride
  12. washThe organic layer was washed with water
  13. dry with materialdried over sodium sulfate
  14. concentrationThe solvent was concentrated under reduced pressure
  15. customthe residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-3c58b77aecd94dd38662a720502eb881
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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