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Tetrahydrofuran → Gamma-secretase modulators

HRID 16352
ノート
印刷プレビュー

反応式

HRID 16352 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

HCID 24781184Gamma-secretase modulators収率 38.2%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-421593376c09495a9ee94f0957f8f9d6
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737141B2

反応ノート

読み込み中…

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