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tert-Butyl hydroperoxide → 3-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-methylsulfinylbenzoylamino]-N-(5-chloropyridin-2-yl)-pyridine-2-carboxamide

HRID 1434830
ノート
印刷プレビュー

反応式

HRID 1434830 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40][CH3:41])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[C:21]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=[O:44].C(OO)(C)(C)C>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40]([CH3:41])=[O:44])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[C:21]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物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 6410tert-Butyl hydroperoxideHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 116999433-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

生成物 1

HCID 579365183-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-methylsulfinylbenzoylamino]-N-(5-chloropyridin-2-yl)-pyridine-2-carboxamide収率 375.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

3-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (2.19 g, 3.66 mmol) was diluted with chloroform (20 mL). Camphorsulfonic acid (179 mg, 0.77 mmol) was added, followed by a solution of t-butyl hydroperoxide (0.75 mL, 7.50 mmol). After stirring overnight, the reaction was concentrated and purified by flash column chromatography (about 225 g silica, 10% EtOAc/CH2Cl2 through 10% MeOH/CH2Cl2) to give the desired product as a white solid (1.775 g, 2.89 mmol, 79%).

後処理

  1. concentrationthe reaction was concentrated
  2. custompurified by flash column chromatography (about 225 g silica, 10% EtOAc/CH2Cl2 through 10% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-1753e29f02fe4bd99aa92056f7444b60
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07615568B2

反応ノート

読み込み中…

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