Trifluoroacetic acid → HCID 57879570, compound

HRID 1673477Notes

Reaction equation

HRID 1673477 reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[CH:29]=[C:28]([N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][CH2:31]2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8]([NH:16][C:17]1[CH:29]=[C:28]([N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][CH2:31]2)[CH:27]=[CH:26][C:18]=1[C:19]([OH:21])=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67342384HCID 67342384, compound

Product 1

HCID 57879570HCID 57879570, compoundYield 78.6%

Procedure

5.0 mL of trifluoroacetic acid solution containing 75 mg of tert-butyl 2-(benzamido)-4-(indolin-1-yl)benzoate was stirred at room temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, ethyl acetate and water were added and pH was adjusted to pH 6.5 with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with water and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Methanol was added to the obtained residue and a solid substance was separated by filtration to obtain 51 mg of 2-(benzamido)-4-(indolin-1-yl)benzoic acid a yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with water
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  7. additionMethanol was added to the obtained residue
  8. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-3681e30cef3449299fa45006aa636d44
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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