Imidazole → HCID 86757080, compound

HRID 1070002Notes

Reaction equation

HRID 1070002 reaction equation
[F:1][C:2]([F:19])([F:18])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10](CO)=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:8]=1)(=[O:5])=[O:4].Cl[Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1.CN(C=[O:37])C>O>[F:19][C:2]([F:1])([F:18])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([O:37][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[C:9]([CH:15]([CH3:16])[CH3:17])[CH:8]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 225688934-Hydroxymethyl-3-isopropyl-phenyl 1,1,1-trifluoro-methanesulfonate2×

Product 1

HCID 86757080HCID 86757080, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-hydroxymethyl-3-isopropyl-phenyl 1,1,1-trifluoro-methansulfonate (Intermediate 149, 760.0 mg, 2.55 mmols), chloro-tert-butyl-dimethylsilane (470.0 mg, 3.18 mmols), and imidazole (225.0 mg, 3.25 mmols) in 6 mL DMF was stirred at 25° C. for 17 hours. The solution was diluted with H2O and extracted with Et2O and the combined organic layers were washed with 10% aqueous HCl, saturated aqueous NaHCO3, H2O, and saturated aqueous NaCl, and dried (MgSO4) before being concentrated under reduced pressure. Column chromatography (2-5% EtOAc-hexanes) afforded 970.0 mg (92%) of the title compound as a colorless oil.

Workup

  1. extractionextracted with Et2O
  2. washthe combined organic layers were washed with 10% aqueous HCl, saturated aqueous NaHCO3, H2O, and saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationbefore being concentrated under reduced pressure

Sources & evidence

ORD record
ord-7b445cfe130648c9890962f1c74042ea
Source dataset
uspto-grants-2001_06
Patent number
US06252090B1

Reaction notes

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