Trifluoroacetic acid → 4-[N'-(2-methoxyphenyl)ureido]-3-methylphenylacetic acid

HRID 354365Notes

Reaction equation

HRID 354365 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:27])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[CH:14][C:13]=1[CH3:26].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:27])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][C:13]=1[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512525tert-butyl 4-[N'-(2-methoxyphenyl)ureido]-3-methylphenylacetate

Product 1

HCID 235122654-[N'-(2-methoxyphenyl)ureido]-3-methylphenylacetic acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N′-(2-methoxyphenyl)ureido]-3-methylphenylacetate (1.32 g, 3.56 mmol) in CH2Cl2 (15 ml) was added trifluoroacetic acid (10 ml), and the resulting mixture was heated under reflux for 30 min. The mixture was concentrated in vacuo and added water to give precipitate which was collected by filtration. The crude solid was recrystallized from EtOH/hexane to give 4-[N′-(2-methoxyphenyl)ureido]-3-methylphenylacetic acid (932 mg, 83%) as a white powder. mp 260-264° C.; 1H-NMR (CD3OD) δ2.30 (s, 3 H), 3.55 (s, 2 H), 4.87 (s, 3 H), 6.87-6.92 (m, 2 H), 6.97-6.99 (m, 2 H), 7.10-7.24 (m, 2 H), 7.53-7.58 (m, 1 H), 8.04 (d, J=7.2 Hz, 1 H); MS (ESI) m/z 314 (M+).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 min
  3. concentrationThe mixture was concentrated in vacuo
  4. additionadded water
  5. customto give precipitate which
  6. filtrationwas collected by filtration
  7. customThe crude solid was recrystallized from EtOH/hexane

Sources & evidence

ORD record
ord-390e8065fe6e43148a8efe04662ed80b
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

Loading…