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

HRID 354353Notes

Reaction equation

HRID 354353 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[CH:13][C:12]=1[CH3:25].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512195tert-butyl 4-[N'-(2-fluorophenyl)ureido]-3-methylphenylacetate

Product 1

HCID 235121124-[N'-(2-fluorophenyl)ureido]-3-methylphenylacetic acidYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N′-(2-fluorophenyl)ureido]-3-methylphenylacetate (1.25 g, 3.49 mmol) in CH2Cl2 (10 ml) was added TFA (10 ml) and the reaction mixture was stirred at room temperature overnight. 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 4-[N′-(2-fluorophenyl)ureido]-3-methylphenylacetic acid (830 mg, 79%) as white needles. 1H-NMR (DMSO-d6) δ2.23 (s, 3 H), 3.47 (s, 2 H), 6.96-7.30 (m, 5 H), 7.74-7.76 (m, 1 H), 8.17-8.20 (m, 1 H), 8.33 (s, 1 H), 8.94 (s, 1 H), 12.27 (br s, 1 H); Anal. Calcd. for C16H15FN2O3: C, 63.57; H, 5.00; N, 9.27; F, 6.28. Found: C, 63.28; H, 5.00; N, 9.14; F, 6.43.

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-909e7d23911b423698c9166cfe52b094
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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