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

HRID 1770642Notes

Reaction equation

HRID 1770642 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([C:15]2[CH2:19][C@:18]([C:24]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:14]=[C:13]([C:15]2[CH2:19][C@:18]([C:24]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727016tert-butyl 2-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoate

Product 1

HCID 867270182-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoate (64.87 mmol, 33 g) in dichloromethane (300 mL) was added trifluoroacetic acid (389.2 mmol, 44.6 g) at 0° C. 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 crude title product which was purified over a silica gel column (eluent: CH2Cl2/EtOAc) to obtain the desired product as pale yellow foam. LCMS (Method GR) RT 1.23 min, [M+H]+ 450/452; 1H-NMR (CDCl3, 400 MHz): 2.7 (s, 3H), 3.70 (d, 2H), 4.10 (d, 2H), 7.60 (s, 3H), 7.01 (d, 1H), 8.15 (d, 2H), 7.01 (d, 1H), 8.15 (d, 2H), 11.40 (s, 1H); 19F-NMR (CDCl3, 376 MHz): −79.38.

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
  8. customto yield crude title product which
  9. customwas purified over a silica gel column (eluent: CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-2f76df525dff49ffa877ecb6f8d99fad
Source dataset
uspto-grants-2016_02
Patent number
US09247740B2

Reaction notes

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