Tert-butyl 2-(benzamido)-4-(2-chloro-6-fluorophenyl)benzoate → 2-(Benzamido)-4-(2-chloro-6-fluorophenyl)benzoic acid

HRID 1673473Notes

Reaction equation

HRID 1673473 reaction equation
[C:1]([NH:9][C:10]1[CH:22]=[C:21]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:30])[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[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:30])[CH:20]=[CH:19][C:11]=1[C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67342982Tert-butyl 2-(benzamido)-4-(2-chloro-6-fluorophenyl)benzoate

Product 1

HCID 578795122-(Benzamido)-4-(2-chloro-6-fluorophenyl)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-(2-chloro-6-fluorophenyl)benzoate and stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and toluene was added. The solvent was evaporated under reduced pressure and the obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 70-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 5.8 mg of 2-(benzamido)-4-(2-chloro-6-fluorophenyl)benzoic acid as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure and toluene
  2. additionwas added
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 70-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record
ord-b7cd85a1066e4ee1867658f8ab1af0c9
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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