Trifluoroacetic acid → HCID 57879548, compound

HRID 1673566Notes

Reaction equation

HRID 1673566 reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][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[CH2:31][CH2:32][CH:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:34][CH2:35]2)[CH:27]=[CH:26][C:18]=1[C:19]([OH:21])=[O:20])(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67343098HCID 67343098, compound

Product 1

HCID 57879548HCID 57879548, compound

Procedure

5.0 mL of trifluoroacetic acid was added to the obtained tert-butyl 2-(benzamido)-4-(4-phenylpiperidin-1-yl)benzoate and stirred at room temperature for 3 hours, 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. Diisopropyl ether was added to the obtained residue and a solid substance was separated by filtration to obtain 20 mg of 2-(benzamido)-4-(4-phenylpiperidin-1-yl)benzoic acid as white 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. additionDiisopropyl ether was added to the obtained residue
  8. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-e878b5d6873f4657adcb9e6bb677880f
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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