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Tetrahydrofuran → Gamma-secretase modulators

HRID 16352
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HRID 16352 반응식
O.[OH-].[Li+].O1CCCC1.C(OP([CH:17]1[C:26](=[O:27])[N:25]2[C@H:20]([CH2:21][O:22][CH2:23][C@H:24]2[C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=2)[CH2:19][CH2:18]1)(=O)OCC)C.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[N:47]1[CH:51]=[C:50]([CH3:52])[N:49]=[CH:48]1)[CH:42]=O>O.C(OCC)(=O)C.C(O)C>[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[N:47]1[CH:51]=[C:50]([CH3:52])[N:49]=[CH:48]1)/[CH:42]=[C:17]1\[CH2:18][CH2:19][C@@H:20]2[N:25]([C:26]\1=[O:27])[C@H:24]([C:28]1[CH:29]=[C:30]([F:36])[C:31]([F:35])=[C:32]([F:34])[CH:33]=1)[CH2:23][O:22][CH2:21]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 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 8857Ethyl Acetate용매

실험 절차

Lithium hydroxide monohydrate (63.4 mg) was added to a solution mixture of tetrahydrofuran (6 mL) and ethanol (2 mL) of [(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonic acid diethyl ester (372 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (229 mg) at room temperature. The resulting reaction solution was stirred at room temperature for 2 hr, and ethyl acetate and water were added thereto. The organic layer was separated, washed with saturated saline, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluting solvent: heptane-ethyl acetate system) to give 163.2 mg of the title compound. The physical property values of this compound were as follows:

후처리

  1. customThe resulting reaction solution
  2. customThe organic layer was separated
  3. washwashed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluting solvent: heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-421593376c09495a9ee94f0957f8f9d6
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737141B2

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