Trifluoroacetic acid → 4-[N'-(2-iodophenyl)ureido]-3-methoxyphenylacetic acid

HRID 354347Notes

Reaction equation

HRID 354347 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:27])[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[O:25][CH3:26].C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:27])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512256tert-butyl 4-[N'-(2-iodophenyl)ureido]-3-methoxyphenylacetate

Product 1

HCID 235123154-[N'-(2-iodophenyl)ureido]-3-methoxyphenylacetic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of tert-butyl 4-[N′-(2-iodophenyl)ureido]-3-methoxyphenylacetate (3.93 g, 8.16 mmol) and TFA (5 ml) in CH2Cl2 (5 ml) was refluxed for 3 h. After cooling to rt, the mixture was concentrated in vacuo and H2O (50 ml) was added to this residue. The resulting precipitate was collected by filtration and purified by column chromatography on silica gel with CHCl3—MeOH (9:1) as eluent to give 4-[N′-(2-iodophenyl)ureido]-3-methoxyphenylacetic acid (2.89 g, 83%) as a pale yellow crystalline powder. 1H-NMR (DMSO-d6) δ3.62 (s, 2 H), 3.88 (s, 3 H), 6.78 (d, J=8.3 Hz, 1 H), 6.83-6.87 (m, 1 H), 6.94 (s, 1 H), 7.32-7.36 (m, 1 H), 7.69 (dd, J=8.3, 1.5 Hz, 1 H), 7.84 (dd, J=8.3, 1.5 Hz, 1 H), 7.97-8.00 (m, 1 H), 8.55 (m, 1H), 8.82 (m, 1 H), 12.26 (br s, 1 H).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationthe mixture was concentrated in vacuo and H2O (50 ml)
  3. additionwas added to this residue
  4. filtrationThe resulting precipitate was collected by filtration
  5. custompurified by column chromatography on silica gel with CHCl3—MeOH (9:1) as eluent

Sources & evidence

ORD record
ord-e937242cb6634b31b0141db1bdbef8c6
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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