Trifluoroacetic acid → HCID 66665000, compound

HRID 874213Notes

Reaction equation

HRID 874213 reaction equation
C([O:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:17][C:16]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)([C:18]([F:21])([F:20])[F:19])[O:15][N:14]2[CH3:30])=[CH:9][C:8]=1[CH3:31])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:29][C:24]1[CH:23]=[C:22]([C:16]2([C:18]([F:20])([F:19])[F:21])[O:15][N:14]([CH3:30])[CH:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:32])=[O:5])=[C:8]([CH3:31])[CH:9]=3)[CH2:17]2)[CH:27]=[C:26]([Cl:28])[CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66664799HCID 66664799, compound

Product 1

HCID 66665000HCID 66665000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-isoxazolidin-3-yl]-2-methyl-benzoic acid tert-butyl ester (Example I4) (0.67 g) in dichloromethane (15 ml) was added trifluoroacetic acid (“TFA”) (1.05 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The dichloromethane was evaporated and ethyl acetate was added. The mixture was washed with water, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give 4-[5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-isoxazolidin-3-yl]-2-methyl-benzoic acid as a mixture of diastereoisomers (0.56 g). 1H-NMR (CDCl3, 400 MHz): 8.05 (m, 1H), 7.45-7.15 (m, 5H), 3.90-3.60 (m, 1H), 3.35-2.60 (m, 9H).

Workup

  1. customThe dichloromethane was evaporated
  2. additionethyl acetate was added
  3. washThe mixture was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-83db34ad5cd14d40b1729ac60b113843
Source dataset
uspto-grants-2015_03
Patent number
US08980892B2

Reaction notes

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