Tert-butyl 2-(3-methylanilino)-4-phenethylbenzoate → 2-(3-Methylanilino)-4-phenethylbenzoic acid

HRID 2191739Notes

Reaction equation

HRID 2191739 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[NH:5][C:6]1[CH:18]=[C:17]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:7]=1[C:8]([O:10]C(C)(C)C)=[O:9]>FC(F)(F)C(O)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[NH:5][C:6]1[CH:18]=[C:17]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:7]=1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 68957121Tert-butyl 2-(3-methylanilino)-4-phenethylbenzoate

Product 1

HCID 576678882-(3-Methylanilino)-4-phenethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid 10 mL was added to the obtained tert-butyl 2-(3-methylanilino)-4-phenethylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 77-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-(3-methylanilino)-4-phenethylbenzoic acid 15 mg of white solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-164b4d9e56cb4365b2f037bebc63fb84
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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