Trifluoroacetic acid → HCID 58508651, compound

HRID 454572Notes

Reaction equation

HRID 454572 reaction equation
FC(F)(F)C(O)=O.C([O:11][C:12]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:13]=1[C:14]([NH:16][C:17]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:33](C(OC(C)(C)C)=O)[CH3:34])[CH:24]=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20])=[O:15])(=O)C>>[OH:11][C:12]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:13]=1[C:14]([NH:16][C:17]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[NH:33][CH3:34])[CH:24]=[CH:23][C:18]=1[C:19]([OH:21])=[O:20])=[O:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66990792HCID 66990792, compound

Product 1

HCID 58508651HCID 58508651, compound

Conditions

Temperature
52.5 °C

Procedure

A trifluoroacetic acid (3.0 mL) solution of the obtained methyl 2-(2-acetoxy-5-methoxybenzamido)-4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)benzoate was stirred at room temperature for 1 hour and 40 minutes. The solvent was evaporated under reduced pressure, and toluene was added to the residue. The solvent was evaporated under reduced pressure, and dioxane (3.0 mL) and a 4 mol/L aqueous solution of sodium hydroxide (0.25 mL) were added to the obtained residue, followed by stirring at 50 to 55° C. for 1 hour and 30 minutes and then at 55 to 60° C. for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and water added thereto. After adjusting the pH to 7.0 with 1 mol/L hydrochloric acid, the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.025 g of 2-(2-hydroxy-5-methoxybenzamido)-4-(2-(methylamino)phenyl)benzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and toluene
  2. additionwas added to the residue
  3. customThe solvent was evaporated under reduced pressure, and dioxane (3.0 mL)
  4. additiona 4 mol/L aqueous solution of sodium hydroxide (0.25 mL) were added to the obtained residue
  5. waitat 55 to 60° C. for 2 hours
  6. custom30 minutes
  7. temperatureThe reaction mixture was cooled to room temperature
  8. additionwater added
  9. customthe solvent was evaporated under reduced pressure
  10. additionWater was added to the obtained residue
  11. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-8edae6d175d1458ca455e26a254a8dcb
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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