Trifluoroacetic acid → HCID 136351071, compound

HRID 1505274Notes

Reaction equation

HRID 1505274 reaction equation
C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17](=[N:18][OH:19])[C:16]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:32])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C.O>[Cl:31][C:26]1[CH:25]=[C:24]([C:16]2([C:20]([F:22])([F:21])[F:23])[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:33])=[O:5])=[C:8]([CH3:32])[CH:9]=3)[C:17]2=[N:18][OH:19])[CH:29]=[C:28]([Cl:30])[CH:27]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 136351072HCID 136351072, compound

Product 1

HCID 136351071HCID 136351071, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-(3,5-dichloro-phenyl)-4-hydroxyimino-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (Example 13.2) (634 mg) in dichloromethane (4 ml) was added trifluoroacetic acid (“TFA”) (0.2 ml) and the reaction mixture was stirred at ambient temperature for 8 hours. Further trifluoroacetic acid (0.2 ml) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and water and the phases were separated. The organic layer was washed successively with water and brine, dried over magnesium sulfate, and concentrated to give 4-[5-(3,5-dichloro-phenyl)-4-hydroxyimino-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (554 mg) as a yellow foam. 1H-NMR (CDCl3, 400 MHz): 8.94 (s, 1H), 8.10 (d, 1H), 7.90 (m, 2H), 7.59 (m, 2H), 7.44 (m, 1H), 2.69 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 16 hours
  2. customthe phases were separated
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64383db338bf409a894c54502b98671b
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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