Trifluoroacetic acid → HCID 23512018, compound

HRID 350430Notes

Reaction equation

HRID 350430 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:28])[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[O:26][CH3:27].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:28])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][C:13]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23511759HCID 23511759, compound

Product 1

HCID 23512018HCID 23512018, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N′-(2-methoxyphenyl)ureido]-3-methoxylphenyl-acetate (2.01 g, 5.20 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. Water was added to the residue to give precipitate, which was collected by filtration. The crude solid was recrystallized from EtOH/hexane to give 4-[N′-(2-methoxyphenyl)ureido]-3-methoxy phenylacetic acid as white powder (1.40 g, 82%). mp 182–185° C.; 1H-NMR (CD3OD) δ 3.55 (s, 2 H), 3.88 (s, 3 H), 3.89 (s, 3 H), 6.80–6.99 (m, 5 H), 7.94 (d, J=8.4 Hz, 1 H), 8.00 (d, J=7.2 Hz, 1 H); MS (ESI) m/z 330 (M+).

Workup

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

Sources & evidence

ORD record
ord-78da5051a3f2446b8053788726856c32
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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