Tert-butyl 2-(2-acetoxybenzamido)-4-phenethylbenzoate → 2-(2-Hydroxybenzamido)-4-phenethylbenzoic acid
Reaction equation
C([O:4][C:5]1[CH:34]=[CH:33][CH:32]=[CH:31][C:6]=1[C:7]([NH:9][C:10]1[CH:22]=[C:21]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:11]=1[C:12]([O:14]C(C)(C)C)=[O:13])=[O:8])(=O)C>FC(F)(F)C(O)=O>[OH:4][C:5]1[CH:34]=[CH:33][CH:32]=[CH:31][C:6]=1[C:7]([NH:9][C:10]1[CH:22]=[C:21]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:20]=[CH:19][C:11]=1[C:12]([OH:14])=[O:13])=[O:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
10 mL of trifluoroacetic acid was added to the obtained tert-butyl 2-(2-acetoxybenzamido)-4-phenethylbenzoate and stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and 0.50 mL of methanol, 0.50 mL of tetrahydrofuran and 10 mg of potassium carbonate were added to the obtained residue sequentially and stirred at room temperature for 3 hours. After insoluble were removed by filtration, 3.0 mL of 10% citric acid aqueous solution was added and a solid; substance was separated, by filtration to obtain 11 mg of 2-(2-hydroxybenzamido)-4-phenethylbenzoic acid as white solid.
Workup
- customThe solvent was evaporated under reduced pressure and 0.50 mL of methanol, 0.50 mL of tetrahydrofuran and 10 mg of potassium carbonate
- additionwere added to the obtained residue sequentially
- stirringstirred at room temperature for 3 hours
- customAfter insoluble were removed by filtration, 3.0 mL of 10% citric acid aqueous solution
- additionwas added
- customsubstance was separated, by filtration
Sources & evidence
- ORD record
- ord-c6074efba396494aa2dde26bd6388a96
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07999132B2
Reaction notes
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