Trifluoroacetic acid → HCID 11950813, compound

HRID 2191858Notes

Reaction equation

HRID 2191858 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:38])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:29]=[C:28]([CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:27]=[CH:26][C:18]=2[C:19]([O:21]C(C)(C)C)=[O:20])=[CH:12][CH:11]=1>>[CH3:38][N:9]([CH3:8])[C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[CH:29]=[C:28]([CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:27]=[CH:26][C:18]=2[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68958347HCID 68958347, compound

Product 1

HCID 11950813HCID 11950813, compound

Procedure

Trifluoroacetic acid 5.0 mL was added to tert-butyl 2-((4-(dimethylamino)phenyl)amino)-4-phenethylbenzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, ethyl acetate and water were added to the obtained residue, and it was adjusted to pH6.5 with saturated sodium hydrogen carbonate aqueous solution. 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. Diisopropyl ether was added to the obtained residue, solid matter was filtrated to give 2-((4-(dimethylamino)phenyl)amino)-4-phenethylbenzoic acid 83 mg of a pale yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure, ethyl acetate and water
  2. additionwere added to the obtained residue, and it
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue, solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-3678e3e3c96446b4af3e9d341d9c08a7
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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