Imidazole → HCID 131718232, compound

HRID 1609075Notes

Reaction equation

HRID 1609075 reaction equation
[F:1][C:2]1[C:3]([CH2:22][CH:23]([OH:25])[CH3:24])=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[NH:5][CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].N1C=CN=C1.[C:31]([Si:35]([CH3:38])([CH3:37])Cl)([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl>[F:1][C:2]1[C:3]([CH2:22][CH:23]([O:25][Si:35]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:38])[CH3:37])[CH3:24])=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[NH:5][CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 14268878HCID 14268878, compound

Product 1

HCID 131718232HCID 131718232, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

14.2 g (40 mmol) of the compound (151) and 3.27 g (48 mmol) of imidazole were added to 100 ml of methylene chloride, and 20 ml of methylene chloride containing 7.23 g (48 mmol) of t-butyldimethylchlorosilane was dropped to the solution through 30 minutes. After the solution was stirred for 2.5 hours at room temperature, it was heated at reflux for 2 hours. 3.27 g of imidazole and 7.23 g of t-butyldimethylchlorosilane were supplemented to the solution, and the solution was heated at reflux for 11 hours. The solution was washed 100 ml of water, 50 ml of aqueous citric acid solution and 50 ml of saturated aqueous sodium hydrogen carbonate solution in this order, and after drying over magnesium sulfate, the solvent was removed by distillation. The solid matter was separated by column chromatography (silica gel 600 g, eluent solvent; chloroform:n-hexane=1:1) to obtain 14.2 g of an oily subject compound (152) in a 76% yield.

Workup

  1. additionwas dropped to the solution through 30 minutes
  2. temperatureit was heated
  3. temperatureat reflux for 2 hours
  4. temperaturethe solution was heated
  5. temperatureat reflux for 11 hours
  6. washThe solution was washed 100 ml of water, 50 ml of aqueous citric acid solution and 50 ml of saturated aqueous sodium hydrogen carbonate solution in this order
  7. dry with materialafter drying over magnesium sulfate
  8. customthe solvent was removed by distillation
  9. customThe solid matter was separated by column chromatography (silica gel 600 g, eluent solvent; chloroform:n-hexane=1:1)

Sources & evidence

ORD record
ord-daccff86dfdb4179b7cd4560c4e4c869
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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