Trifluoroacetic acid → HCID 46853603, compound

HRID 454537Notes

Reaction equation

HRID 454537 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:36]=[C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[CH:34]=[CH:33][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][CH:28]=2)[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:36]=[C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][C:15]=1[C:16]([OH:18])=[O:17])=[O:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508678HCID 58508678, compound

Product 1

HCID 46853603HCID 46853603, compoundYield 74.4%

Procedure

A trifluoroacetic acid (5 mL) solution of the obtained tert-butyl 2-(2-hydroxy-4-(pyridin-2-yl)benzamido)-4-phenylbenzoate (0.11 g) was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the obtained residue. After adjusting the pH to 6.0 with a saturated aqueous solution of sodium bicarbonate, the solid substance was collected by filtration. Water (4 mL), methanol (4 mL), and dioxane (4 mL) were added to the obtained solid substance, and carbon dioxide gas was introduced thereinto at room temperature. The solvent was evaporated under reduced pressure, and water was added to the obtained residue. The solid substance was collected by filtration to obtain 0.072 g of 2-(2-hydroxy-4-(pyridin-2-yl)benzamido)-4-phenylbenzoic acid as a light yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added to the obtained residue
  3. filtrationthe solid substance was collected by filtration
  4. additionWater (4 mL), methanol (4 mL), and dioxane (4 mL) were added to the obtained solid substance, and carbon dioxide gas
  5. additionwas introduced
  6. customat room temperature
  7. customThe solvent was evaporated under reduced pressure, and water
  8. additionwas added to the obtained residue
  9. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-a3ec804da8494fe3b2fe22b0ba2d3de4
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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