Benzofuran-2-carboxylic acid → HCID 67109825、化合物

HRID 29453

反応式

HRID 29453 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].[C:13]([O:17][C:18](=[O:40])[CH:19]([NH:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH:20]([CH3:22])[CH3:21])([CH3:16])([CH3:15])[CH3:14]>ClCCl.CN(C)C1C=CN=CC=1>[C:13]([O:17][C:18]([CH:19]([NH:23][S:24]([C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([O:11][C:10]([C:2]3[O:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[CH:3]=3)=[O:12])=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)(=[O:25])=[O:26])[CH:20]([CH3:22])[CH3:21])=[O:40])([CH3:15])([CH3:16])[CH3:14]

参加物

5

反応物 2

HCID 10331Benzofuran-2-carboxylic acidHCID 671099642-(4'-Hydroxy-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl ester

生成物 1

HCID 67109825HCID 67109825、化合物収率 31%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To benzofuran-2-carboxylic acid (0.401 g, 2.47 mmol, 1 equiv.) dissolved in dry dichloromethane (50 mL) was added dicyclohexylcarbidiimide (1.019 g, 4.94 mmol, 2 equiv) and the mixture was stirred under nitrogen for 15 minutes. Then 2-(4′-hydroxy-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl ester (1.0 g, 2.47 mmol, 1 equiv., Example 134, Step 1) was introduced to the reaction mixture, followed by the addition of 4-dimethylamino pyridine (0.050 g, 0.41 mmol). The mixture was allowed to stir at room temperature overnight. The reaction mixture was then diluted with dichloromethane, washed with water and brine. The organic layer was dried over magnesium sulfate and the solvent was concentrated in vacuo. The residue was dissolved in ethyl acetate and purified by column chromatography on silica gel eluting with 20% ethyl acetate/hexane to afford 325 mg of benzofuran-2-carboxylic acid 4′-(1-tert-butoxycarbonyl-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester in 31% yield. 1H NMR (400 MHz, CDCl3) δ ppm 0.87 (d, J=6.82 Hz, 3 H) 1.03 (d, J=6.82 Hz, 3 H) 1.21 (s, 9 H) 2.07 (m, 1 H) 3.68 (dd, J=9.85, 4.55 Hz, 1 H) 5.15 (d, J=9.85 Hz, 1 H) 7.37 (m, 3 H) 7.53 (t, J=7.83 Hz, 1 H) 7.66 (m, 5 H) 7.77 (m, 2 H) 7.92 (d, J=8.34 Hz, 2 H).

後処理

  1. additionwas added dicyclohexylcarbidiimide (1.019 g, 4.94 mmol, 2 equiv)
  2. stirringto stir at room temperature overnight
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationthe solvent was concentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. custompurified by column chromatography on silica gel eluting with 20% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-12c3ac35267f4083a7b2601d61d8b6da
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

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