Imidazole → HCID 131718232, compound

HRID 1656751Notes

Reaction equation

HRID 1656751 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 chlorideHCID 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-butyldimethylehlorosilane 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 5% 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 5% 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-61790c2be4ac4c14a8e134a2e4e6b87d
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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