Trifluoroacetic acid → HCID 57879388, compound

HRID 1673415Notes

Reaction equation

HRID 1673415 reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[CH:29]=[C:28]([NH:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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]([NH:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=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 67343242HCID 67343242, compound

Product 1

HCID 57879388HCID 57879388, compoundYield 74.2%

Procedure

1.0 mL of trifluoroacetic acid solution containing 0.11 g of tert-butyl 2-(benzamido)-4-((3-phenylpropyl)amino)benzoate was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and ethyl acetate and water were added and pH was adjusted to pH 6.3 with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure, Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 71 mg of 2-(benzamido)-4-((3-phenylpropyl)amino)benzoic acid as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure and 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 a saturated sodium chloride aqueous solution
  6. customthe solvent was evaporated under reduced pressure, Hexane and diisopropyl ether
  7. additionwere added to the obtained residue
  8. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-7647e856bdce4c009e37997e1c62f3d1
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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