Tert-butyl 2-(benzamido)-4-(3-(hydroxymethyl)phenyl)benzoate → 2-(Benzamido)-4-(3-(hydroxymethyl)phenyl)benzoic acid

HRID 1673461Notes

Reaction equation

HRID 1673461 reaction equation
[C:1]([NH:9][C:10]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][OH:30])[CH:24]=2)[CH:20]=[CH:19][C:11]=1[C:12]([O:14]C(C)(C)C)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[C:1]([NH:9][C:10]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][OH:30])[CH:24]=2)[CH:20]=[CH:19][C:11]=1[C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67343132Tert-butyl 2-(benzamido)-4-(3-(hydroxymethyl)phenyl)benzoate

Product 1

HCID 578795362-(Benzamido)-4-(3-(hydroxymethyl)phenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

10 mL of trifluoroacetic acid was added to the obtained tert-butyl 2-(benzamido)-4-(3-(hydroxymethyl)phenyl)benzoate and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and the obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile 0.1% trifluoroacetic acid aqueous solution] to obtain 12 mg of 2-(benzamido)-4-(3-(hydroxymethyl)phenyl)benzoic acid as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile 0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record
ord-817de7732ee24bd8bb541cbce6f7bbdb
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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