tert-butyl 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoate → 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoic acid

HRID 1673503Notes

Reaction equation

HRID 1673503 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:28]=[C:27]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=[CH:25][C:17]=2[C:18]([O:20]C(C)(C)C)=[O:19])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:28]=[C:27]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=[CH:25][C:17]=2[C:18]([OH:20])=[O:19])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 67343538tert-butyl 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoate

Product 1

HCID 578793012-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

10 mL of trifluoroacetic acid was added to the obtained tert-butyl 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoate and stirred at room temperature for 2 hours. 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 34 mg of 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoic 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-6cd57b0258934b69952c7d88976bc67d
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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