Triethylamine → HCID 22259333, compound

HRID 1610987Notes

Reaction equation

HRID 1610987 reaction equation
C(N(CC)CC)C.P(OC)(OC)OC.[F:15][C:16]([F:22])([F:21])[S:17](Cl)(=[O:19])=[O:18].[F:23][C:24]([F:58])([F:57])[C:25]1[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]2[O:34][CH:35]=[C:36]([CH2:38][O:39][C:40]3[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][CH2:48][CH2:49][N:50]4[CH:54]=[CH:53][N:52]=[C:51]4[CH2:55]O)=[CH:42][CH:41]=3)[N:37]=2)=[CH:27][CH:26]=1>C1COCC1.O>[F:57][C:24]([F:23])([F:58])[C:25]1[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]2[O:34][CH:35]=[C:36]([CH2:38][O:39][C:40]3[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][CH2:48][CH2:49][N:50]4[CH:54]=[CH:53][N:52]=[C:51]4[CH2:55][S:17]([C:16]([F:22])([F:21])[F:15])(=[O:19])=[O:18])=[CH:42][CH:41]=3)[N:37]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8472Trimethyl phosphiteHCID 79000Trifluoromethanesulfonyl chlorideHCID 22259311HCID 22259311, compound

Product 1

HCID 22259333HCID 22259333, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (91.0 μl), trimethyl phosphite (77.0 μl) and trifluoromethanesulfonyl chloride (69.5 μl) were added to a solution of [1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]methanol (250 mg, 0.503 mmol) in THF (5 ml) at −30° C., and the mixture was stirred at the same temperature for 20 min and at room temperature for 1 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1) and recrystallized from ethyl acetate-hexane to give the titled compound (38 mg) as a colorless crystal powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fcfbd5f5cd714954aed96d76accda88f
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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