Trifluoroacetic acid → 3-(4-(3-Fluoroazetidin-3-yl)phenyl)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

HRID 1961529Notes

Reaction equation

HRID 1961529 reaction equation
[F:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:23][C:22]([C:28]4[CH:33]=[C:32]([Cl:34])[C:31]([Cl:35])=[C:30]([Cl:36])[CH:29]=4)([C:24]([F:27])([F:26])[F:25])[O:21][N:20]=3)=[CH:15][CH:14]=2)[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:23][C:22]([C:28]4[CH:33]=[C:32]([Cl:34])[C:31]([Cl:35])=[C:30]([Cl:36])[CH:29]=4)([C:24]([F:26])([F:27])[F:25])[O:21][N:20]=3)=[CH:15][CH:14]=2)[CH2:3][NH:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 78146950Tert-butyl 3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidine-1-carboxylate

Product 1

HCID 781477423-(4-(3-Fluoroazetidin-3-yl)phenyl)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 250 mg of tert-butyl 3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidine-1-carboxylate (Preparation 8) in 2 mL CH2Cl2 was added 1 mL of trifluoroacetic acid. The reaction was stirred overnight under a positive pressure of nitrogen. The reaction was concentrated. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted 2× with EtOAc (20 mL). The combined organics were dried over Na2SO4 and condensed to yield 188 mg of a film. TLC shows much more polar spot. The crude product was carried on to the next reactions. MS calculated for (C19H13Cl3F4N2O), 466.00; found 467.9 M+H

Workup

  1. concentrationThe reaction was concentrated
  2. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted 2× with EtOAc (20 mL)
  4. dry with materialThe combined organics were dried over Na2SO4 and condensed
  5. customto yield 188 mg of a film

Sources & evidence

ORD record
ord-d020447989614db78bde0824bc4a66a6
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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