Trifluoroacetic acid → HCID 66665000, compound

HRID 1505239Notes

Reaction equation

HRID 1505239 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 4.4) (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-141fc2922a1946cf82e1c9c78f184060
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

Loading…