Trifluoroacetic acid → 2-((2-(Dimethylamino)phenyl)amino)-4-phenethylbenzoic acid
Reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:38])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]1[CH:29]=[C:28]([CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20]>>[CH3:38][N:9]([CH3:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]1[CH:29]=[C:28]([CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:18]=1[C:19]([OH:21])=[O:20]Participants
Procedure
Trifluoroacetic acid 5.0 mL was added to the obtained tert-butyl 2-((2-(dimethylamino)phenyl)amino)-4-phenethylbenzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 50-85% acetonitrile/0.1% trifluoroacetic acid aqueous solution], and ethyl acetate, water and saturated sodium hydrogen carbonate aqueous solution were added to it, and it was adjusted to pH6.5. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane was added to the obtained residue, and solid matter was filtrated to give 2-((2-(dimethylamino)phenyl)amino)-4-phenethylbenzoic acid 7.0 mg of a yellow solid.
Workup
- customThe solvent was removed under reduced pressure
- additionwere added to it, and it
- customThe organic layer was separated
- washafter washing with saturated sodium chloride aqueous solution
- customthe solvent was removed under reduced pressure
- additionHexane was added to the obtained residue, and solid matter
- filtrationwas filtrated
Sources & evidence
- ORD record
- ord-79807aa4e8b248cebfbcc24c3c976d8b
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08327467B2
Reaction notes
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