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

HRID 354347ノート

反応式

HRID 354347 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e937242cb6634b31b0141db1bdbef8c6
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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