Trifluoroacetic acid → HCID 46853620, compound

HRID 454559Notes

Reaction equation

HRID 454559 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[CH:35][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH:24]=[CH:23][C:15]=1[C:16]([O:18]C(C)(C)C)=[O:17])=[O:12]>>[OH:8][C:9]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[CH:35][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH:24]=[CH:23][C:15]=1[C:16]([OH:18])=[O:17])=[O:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508487HCID 58508487, compound

Product 1

HCID 46853620HCID 46853620, compound

Procedure

A trifluoroacetic acid (4.0 mL) solution of the obtained tert-butyl 2-(2-hydroxy-5-(pyridin-3-yl)benzamido)-4-(2-methoxyphenyl)benzoate was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and toluene was added to the residue. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration. Dioxane (2.0 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.49 mL) were added to the obtained solid substance, followed by stirring at room temperature for 45 minutes. A 10% aqueous solution of citric acid was added to the reaction mixture, and the solid substance was collected by filtration. Ethanol and water were added to the obtained solid substance, and the solid substance was collected by filtration to obtain 0.053 g of 2-(2-hydroxy-5-(pyridin-3-yl)benzamido)-4-(2-methoxyphenyl)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 diisopropyl ether
  4. additionwas added to the obtained residue
  5. filtrationThe solid substance was collected by filtration
  6. additionDioxane (2.0 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.49 mL) were added to the obtained solid substance
  7. additionA 10% aqueous solution of citric acid was added to the reaction mixture
  8. filtrationthe solid substance was collected by filtration
  9. additionEthanol and water were added to the obtained solid substance
  10. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-4a57dcc2f14a4c56a58ce2186b80e707
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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