Trifluoroacetic acid → HCID 18459163, compound

HRID 2305239Notes

Reaction equation

HRID 2305239 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH:17]=[C:16]2[C:21]2[O:22][C:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:25]=2)[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:26]1([C:24]2[N:25]=[C:21]([C:16]3[CH:15]([CH2:14][C:10]4[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=4)[CH2:20][CH2:19][CH2:18][CH:17]=3)[O:22][C:23]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70105059HCID 70105059, compound

Product 1

HCID 18459163HCID 18459163, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenyl}carbamic acid tert-butyl ester (2.34 g, 4.62 mmol) in methylene chloride (25 ml) was added trifluoroacetic acid (7 ml) at 5° C. and the mixture was stirred at room temperature for 1.5 hour. After evaporation, the residue was dissolved in EtOAc, and saturated sodium hydrogencarbonate solution was added thereto under ice-cooling. The mixture was extracted with EtOAc, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 3:1 elution) to give 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-y]methyl}phenylamine (1.74 g, 93%).

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in EtOAc
  3. additionsaturated sodium hydrogencarbonate solution was added
  4. temperatureunder ice-cooling
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 3:1 elution)

Sources & evidence

ORD record
ord-1131caa9907e4b158f09fae651f34532
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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