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Ethyl Acetate → Gamma-secretase modulators

HRID 553960
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HRID 553960 반응식
O.[OH-].[Li+].[O:4]=[C:5]1[N:14]2[C@H:9]([CH2:10][O:11][CH2:12][C@H:13]2[C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=2)[CH2:8][CH2:7][CH:6]1P(=O)(OCC)OCC.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1)[CH:37]=O.C(OCC)(=O)C>O1CCCC1.C(O)C.O>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1)/[CH:37]=[C:6]1\[CH2:7][CH2:8][C@@H:9]2[N:14]([C:5]\1=[O:4])[C@H:13]([C:15]1[CH:16]=[C:17]([F:23])[C:18]([F:22])=[C:19]([F:21])[CH:20]=1)[CH2:12][O:11][CH2:10]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612713diethyl[(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonate

생성물 1

HCID 24781184Gamma-secretase modulators수율 38.2%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hydroxide monohydrate (63.4 mg) was added to a mixed solution of diethyl [(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonate (372 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (229 mg) in tetrahydrofuran (6 mL) and ethanol (2 mL) at room temperature, and the reaction solution was stirred at room temperature for two hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) to obtain 163.2 mg of the title compound.

후처리

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-0ab6a1af2f6c487483d219b1035da2a7
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08048878B2

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