Trifluoroacetic acid → 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoic acid

HRID 1770646Notes

Reaction equation

HRID 1770646 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:10]2([C:29]([F:32])([F:31])[F:30])[O:14][N:13]=[C:12]([C:15]3[CH:27]=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[C:17]([CH3:28])[CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:10]2([C:29]([F:31])([F:32])[F:30])[O:14][N:13]=[C:12]([C:15]3[CH:27]=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH3:28])[CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727020tert-butyl 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoate

Product 1

HCID 867270224-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL vessel was charged with tert-butyl 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoate (3.1 g, 6.3 mmol) and dissolved in CH2Cl2 (30 mL) and then cooled down to 0° C. To this mixture 2,2,2-trifluoroacetic acid (4.3 g, 38 mmol) was added over 10 min. After addition the reaction was brought to room temperature and the mixture stirred over night after which time LC-MS analysis showed a complete conversion. The crude mixture was concentrated and the residue dissolved in 300 mL of ethylacetate, washed with brine, dried over MgSO4 and evaporated to yield 2.7 g of the crude title product which was directly used for the step D.

Workup

  1. additionAfter addition the reaction
  2. customwas brought to room temperature
  3. concentrationThe crude mixture was concentrated
  4. dissolutionthe residue dissolved in 300 mL of ethylacetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-00927d1028cb46409dd026767b3a833b
Source dataset
uspto-grants-2016_02
Patent number
US09247740B2

Reaction notes

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