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Acetic Acid → (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylic acid

HRID 390590
ノート
印刷プレビュー

反応式

HRID 390590 の反応式
[OH-].[Li+].[CH2:3]([O:5]/[C:6](=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:36])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])[N:20]=2)=[CH:15][CH:14]=1)/[C:7]([O:9]CC)=[O:8])[CH3:4].C(O)(=O)C.O>O1CCCC1.C(OCC)(=O)C>[CH2:3]([O:5]/[C:6](=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:36])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])[N:20]=2)=[CH:15][CH:14]=1)/[C:7]([OH:9])=[O:8])[CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 16224918ethyl (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylate

生成物 1

HCID 16225328(Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylic acid収率 37%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
68 °C

実験手順

0.93 mL (0.93 mmol) of aqueous 1 M lithium hydroxide solution is added to a solution of 0.29 g (0.62 mmol) of ethyl (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylate in 8 mL of tetrahydrofuran. The reaction mixture is stirred at 68° C. for 18 hours. After cooling, the reaction is worked up by addition of 0.93 mL (0.93 mmol) of aqueous 1 M acetic acid solution and 10 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. After filtration, the solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture to give 0.10 g (37%) of (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylic acid in the form of a white solid.

後処理

  1. temperatureAfter cooling
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvents are evaporated off
  6. customThe crude product obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 60/40 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-8547d856cdb8409bb12efb9f291aed57
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08383652B2

反応ノート

読み込み中…

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