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Ethyl Acetate → ethyl 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoate

HRID 20561
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HRID 20561 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([O:24][C@@H:25]([CH3:28])[CH2:26][OH:27])[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12].[CH2:29]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36](F)=[CH:35][CH:34]=1)[CH3:30].C(OCC)(=O)C>CC(N(C)C)=O>[OH:27][CH2:26][C@H:25]([CH3:28])[O:24][C:22]1[CH:23]=[C:8]([CH:9]=[C:10]([C:11]([NH:13][C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=2)=[O:12])[CH:21]=1)[O:7][C:36]1[CH:37]=[CH:38][C:33]([C:32]([O:31][CH2:29][CH3:30])=[O:40])=[CH:34][CH:35]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 591271143-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

생성물 1

HCID 59346869ethyl 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoate수율 3.1%

시약·촉매·용매

1
HCID 31374Dimethylacetamide용매

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온도
130 °C

실험 절차

Caesium carbonate (8.45 g, 26 mmol) was added to a mixture of 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (4 g, 13 mmol) and ethyl-4-fluorobenzoate (2.33 g, 13 mmol) in dimethylacetamide (70 mL) and the stirred mixture heated at 130° C. for 72 hours. The mixture was allowed to reach RT and ethyl acetate (100 mL) added. The mixture was washed with water (5×40 mL), brine (40 mL), dried (MgSO4), filtered, and reduced in vacuo. The residue was chromatographed on silica, eluting with a gradient of 50% ethyl acetate in isohexane, to give the desired compound (0.18 g)

후처리

  1. customto reach RT
  2. washThe mixture was washed with water (5×40 mL), brine (40 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe residue was chromatographed on silica
  6. washeluting with a gradient of 50% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-c641fca714d7436f9429b7f80fe78e04
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745475B2

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