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

HRID 354347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354347
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 235123154-[N'-(2-iodophenyl)ureido]-3-methoxyphenylacetic acidAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e937242cb6634b31b0141db1bdbef8c6
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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