Trifluoroacetic acid → HCID 67196075, compound

HRID 547449Notes

Reaction equation

HRID 547449 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:20]=2[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][N:32]=2)=[O:17])=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])O.[Na+]>>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:20]=2[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][N:32]=2)=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67198432HCID 67198432, compound

Product 1

HCID 67196075HCID 67196075, compoundYield 51.1%

Procedure

To 59 mg of 5-[(4-t-butoxycarbonylaminophenyl)acetylamino]-3-(4-fluorophenyl)-4-(4-pyrimidinyl)isoxazole, 1 mL of TFA was added under cooling with ice, and the temperature was raised to room temperature, followed by 20 minutes' stirring. The reaction solution was neutralized with saturated aqueous sodium hydrogencarbonate solution under cooling with ice, and extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and removed of the solvent by distillation under reduced pressure. The residue was washed with diethylether-hexane to provide 24 mg (yield: 51%) of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customremoved of the solvent by distillation under reduced pressure
  7. washThe residue was washed with diethylether-hexane

Sources & evidence

ORD record
ord-808e14feecaa419d835afe1f281ff5ae
Source dataset
uspto-grants-2011_05
Patent number
US07939536B2

Reaction notes

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