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

HRID 354347노트

반응식

HRID 354347 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e937242cb6634b31b0141db1bdbef8c6
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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