Imidazole → HCID 58026139, compound

HRID 2387320Notes

Reaction equation

HRID 2387320 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([CH3:23])([CH3:22])[CH2:12][C@:13]([OH:21])([C:17]([F:20])([F:19])[F:18])[CH2:14][C:15]#[CH:16])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N1C=CN=C1.[Si:29](Cl)([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31]>CN(C=O)C>[CH3:22][C:11]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([CH3:23])[CH2:12][C@:13]([O:21][Si:29]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31])([C:17]([F:19])([F:20])[F:18])[CH2:14][C:15]#[CH:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 58026119HCID 58026119, compound

Product 1

HCID 58026139HCID 58026139, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 10.6 g (0.032 mol) of 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzoic acid and 17.8 g (0.026 mol) of imidazole in 70 mL of DMF was added 75.6 mL (0.45 mol) of TESCl. The reaction mixture was stirred at 100° C. for 3 days. Volatiles were removed in vacuo, the reaction mixture was cooled to 10° C. with an ice bath, and 1 L of 1 N HCl was added. The ice bath was removed and the mixture was stirred at room temperature for 2 hours. Ethyl acetate was added and the mixture was washed with 1 N HCl, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. 200 mL of 1 N HCl is added and stirred for 1 hour. Ethyl acetate was added and the mixture was washed with 1 N HCl, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-((S)-1,1-dimethyl-3-triethylsilanyloxy-3-trifluoromethylhex-5-ynyl)-5-fluorobenzoic acid.

Workup

  1. customVolatiles were removed in vacuo
  2. temperaturethe reaction mixture was cooled to 10° C. with an ice bath
  3. addition1 L of 1 N HCl was added
  4. customThe ice bath was removed
  5. stirringthe mixture was stirred at room temperature for 2 hours
  6. additionEthyl acetate was added
  7. washthe mixture was washed with 1 N HCl, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. addition200 mL of 1 N HCl is added
  12. stirringstirred for 1 hour
  13. additionEthyl acetate was added
  14. washthe mixture was washed with 1 N HCl, brine
  15. dry with materialdried over sodium sulfate
  16. filtrationfiltered
  17. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9f4898207b449a89fe257de99c5570d
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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