Trifluoroacetic acid → 3-methoxy-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetic acid

HRID 354357Notes

Reaction equation

HRID 354357 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([OH:26])=[O:25])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512196tertbutyl 3-methoxy-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

Product 1

HCID 235120673-methoxy-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-methoxy-4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.11 g, 2.62 mmol) in CH2Cl2 (10 ml) was added TFA (10 ml), and the reaction mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated to a small volume and poured into ice-H2O. The resulting precipitate was collected under a reduced pressure and the crude solid was recrystallized from MeOH—CHCl3—IPE to give 3-methoxy-4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetic acid (839 mg, 87%) as a white crystalline powder. mp 218-220° C.; 1H-NMR (DMSO-d6) δ3.51 (s, 2 H), 3.87 (s, 3 H), 6.76-6.79 (m, 1 H), 6.93-6.94 (m, 1 H), 7.27-7.30 (m, 1 H), 7.61-7.69 (m, 2 H), 7.82-7.84 (m, 1 H), 7.97-7.99 (m, 1 H), 8.71 (s, 1 H), 8.89 (s, 1 H), 12.30 (br s, 1 H); Anal. Calcd. for C17H15F3N2O4: C, 55.44; H, 4.11; N, 7.61; F, 15.47. Found: C, 55.30; H, 4.08; N, 7.63; F, 15.13.

Workup

  1. concentrationThe reaction mixture was concentrated to a small volume
  2. additionpoured into ice-H2O
  3. customThe resulting precipitate was collected under a reduced pressure
  4. customthe crude solid was recrystallized from MeOH—CHCl3—IPE

Sources & evidence

ORD record
ord-51cdc11978464155b38a5eec2a4d27c1
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

Loading…