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Dimethylformamide → (S)-2-{4'-[(5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

HRID 29415
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HRID 29415 반응식
C(O[C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[C:12]([OH:19])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.CCN=C=NCCCN(C)C.[CH3:31][O:32][C:33](=[O:55])[C@@H:34]([NH:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)=[CH:44][CH:43]=1)(=[O:41])=[O:40])[CH:35]([CH3:37])[CH3:36].CN(C=O)C>[Cl-].[Na+].O>[CH3:31][O:32][C:33](=[O:55])[C@@H:34]([NH:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:49]=[CH:50][C:51]([NH:54][C:4]([C:6]3[O:7][C:8]4[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[C:12]([OH:19])[C:9]=4[C:10]=3[CH3:11])=[O:5])=[CH:52][CH:53]=2)=[CH:44][CH:43]=1)(=[O:41])=[O:40])[CH:35]([CH3:37])[CH3:36]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 20205101Ethyl 5-acetyl-4-hydroxy-3-methylbenzofuran-2-carboxylateHCID 59847687(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester

생성물 1

HCID 68716407(S)-2-{4'-[(5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester
수율 11.5%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

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온도
65 °C

실험 절차

To 70 mg (0.3 mmol) of 5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester was added 115 mg (2 eq) EDCI, 109 mg (1 eq) of (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester and 2 mL of DMF. The mixture was stirred at 65° C. overnight. The reaction mixture was poured into brine, and extracted with dichloromethane. The organic solution was washed with 2N HCl and water. Removal of the solvents under vacuum gave crude product, which was purified by column chromatography on silica gel to give 20 mg (10% yield) of (S)-2-{4′-[(5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester as a white solid.

후처리

  1. extractionextracted with dichloromethane
  2. washThe organic solution was washed with 2N HCl and water
  3. customRemoval of the solvents under vacuum
  4. customgave crude product, which
  5. customwas purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-4716ed3695924c9493864b3bdc74a100
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07420001B2

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