Trifluoroacetic acid → HCID 23511783, compound

HRID 354370Notes

Reaction equation

HRID 354370 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=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].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=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 23511810HCID 23511810, compound

Product 1

HCID 23511783HCID 23511783, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N′-(2,6-dichlorophenyl)ureido]-3-methoxyphenylacetate (2.27 g, 5.34 mmol) in CH2Cl2 (50 ml) was added TFA (20 ml) at room temperature. After 2 h string, the mixture was concentrated in vacuo. The residue was triturated by the addition of water, to give 4-[N′-(2,6-dichlorophenyl)ureido]-3-methoxyphenylacetic acid (1.50 g, 76%) as a colorless powder. mp 246-249° C. (dec.); 1H-NMR (DMSO-d6) δ3.49 (s, 2H), 3.88 (s, 3H), 6.75 (d, J=8.3 Hz, 1H), 6.93 (s, 1H), 7.30 (t, J=7.8 Hz, 1H), 7.52 (d, J=8.0 Hz, 2H), 7.97 (d, J=8.0 Hz, 1H), 8.40 (s, 1H), 8.86 (s, 1H), 12.23 (br, 1H); MS (ESI) m/z 369 (M++1), 371 (M++3), 373 (M++5).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was triturated by the addition of water

Sources & evidence

ORD record
ord-6f435c229a7d4d3580c233b9c4c1a539
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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