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

HRID 354365노트

반응식

HRID 354365 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:27])[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[CH3:26].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:27])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][C:13]=1[CH3:26]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 23512525tert-butyl 4-[N'-(2-methoxyphenyl)ureido]-3-methylphenylacetate

생성물 1

HCID 235122654-[N'-(2-methoxyphenyl)ureido]-3-methylphenylacetic acid수율 83.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of tert-butyl 4-[N′-(2-methoxyphenyl)ureido]-3-methylphenylacetate (1.32 g, 3.56 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 and added water to give precipitate which was collected by filtration. The crude solid was recrystallized from EtOH/hexane to give 4-[N′-(2-methoxyphenyl)ureido]-3-methylphenylacetic acid (932 mg, 83%) as a white powder. mp 260-264° C.; 1H-NMR (CD3OD) δ2.30 (s, 3 H), 3.55 (s, 2 H), 4.87 (s, 3 H), 6.87-6.92 (m, 2 H), 6.97-6.99 (m, 2 H), 7.10-7.24 (m, 2 H), 7.53-7.58 (m, 1 H), 8.04 (d, J=7.2 Hz, 1 H); MS (ESI) m/z 314 (M+).

후처리

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

출처 및 근거

ORD 기록
ord-390e8065fe6e43148a8efe04662ed80b
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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