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Hydrogen Bromide → 6-{(E)-1-(4-Chlorophenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-cyclopropylpyridin-2(1H)-one

HRID 70630
ノート
印刷プレビュー

反応式

HRID 70630 の反応式
O1CCOCC1.Br.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[C:23]2[CH:28]=[CH:27][C:26]([CH:29]3[CH2:31][CH2:30]3)=[C:25]([O:32]C)[N:24]=2)=[CH:16]\[C@@H:17]2[NH:21][C:20](=[O:22])[CH2:19][CH2:18]2)=[CH:11][CH:10]=1>O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:23]2[NH:24][C:25](=[O:32])[C:26]([CH:29]3[CH2:31][CH2:30]3)=[CH:27][CH:28]=2)=[CH:16]\[C@H:17]2[CH2:18][CH2:19][C:20](=[O:22])[NH:21]2)=[CH:13][CH:14]=1
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

5

反応物 3

HCID 260Hydrogen BromideHCID 312751,4-DioxaneHCID 67399304(5R)-5-[(E)-2-(4-chlorophenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

生成物 1

HCID 584526046-{(E)-1-(4-Chlorophenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-cyclopropylpyridin-2(1H)-one収率 68%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

1,4-Dioxane (4 mL) and 48% hydrobromic acid (2 mL) were added to (5R)-5-[(E)-2-(4-chlorophenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (250 mg), and the mixture was stirred at 65° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→90:10) to give the title compound as a colorless powder (65 mg, 68% (two steps)).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→90:10)

出典と根拠

ORDレコード
ord-18ace6d546a04cda8fd5222d3300774f
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

反応ノート

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