Trifluoroacetic acid → HCID 58508847, compound

HRID 454615Notes

Reaction equation

HRID 454615 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:36]=[C:35]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]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]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]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]([OH:18])=[O:17])=[O:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508424HCID 58508424, compound

Product 1

HCID 58508847HCID 58508847, compoundYield 85.1%

Procedure

Trifluoroacetic acid (5.0 mL) was added to the obtained tert-butyl 2-(2-hydroxy-4-(piperidin-1-yl)benzamido)-4-phenylbenzoate (0.084 g), followed by stirring at room temperature for 4 hours. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the residue, followed by adjusting the pH to 6.5 with a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration to obtain 0.063 g of 2-(2-hydroxy-4-(piperidin-1-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 residue
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the obtained residue
  8. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-9404899c4f204c1d9aae8406529b32ca
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…