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Benzofuran-2-carboxylic acid → Benzofuran-2-carboxylic acid 4'-(1-tert-butoxycarbonyl-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester

HRID 29453
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HRID 29453 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

HCID 67109825Benzofuran-2-carboxylic acid 4'-(1-tert-butoxycarbonyl-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester수율 31%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매
2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-12c3ac35267f4083a7b2601d61d8b6da
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07420001B2

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