Ethanol → (E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

HRID 1362646노트

반응식

HRID 1362646 반응식
C(O)C.C([O:6][C:7](=O)/[C:8](=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]2)=[C:26]([O:36][CH3:37])[CH:25]=1)/[CH2:9][CH2:10][CH2:11][NH:12][C@@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@@H:14]1[OH:22])C.[OH-].[Na+].O>C(OCC)(=O)C>[OH:22][C@H:14]1[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:13]1[N:12]1[CH2:11][CH2:10][CH2:9]/[C:8](=[CH:23]\[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)=[C:26]([O:36][CH3:37])[CH:25]=2)/[C:7]1=[O:6]

참가 물질

6

반응물 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 66961755(E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl ester

생성물 1

HCID 59170845(E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one수율 72.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To an ethanol (2.0 mL) solution of (E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl ester (120 mg), 2N sodium hydroxide solution (1.0 mL) was added. After carrying out heat-refluxing of the reaction solution for 30 minutes and confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate=1:1->ethyl acetate->ethyl acetate:ethanol=10:1), and 78.9 mg of the title compound was obtained.

후처리

  1. temperatureAfter carrying out heat-refluxing of the reaction solution for 30 minutes
  2. additionwere added to the reaction solution
  3. customthe organic layer was partitioned
  4. washAfter the obtained organic layer was washed with a saturated saline solution, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate=1:1->ethyl acetate->ethyl acetate:ethanol=10:1)

출처 및 근거

ORD 기록
ord-aede15d815644e31acaaaa547fdf03b3
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880009B2

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