Dibutyltin dichloride → 3-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-thiophene-2-carboxylic acid methyl ester

HRID 579186ノート

反応式

HRID 579186 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[CH2:11]([O:13][C:14](=[O:26])[CH2:15][CH2:16][CH2:17][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=O)[CH3:12].C1([SiH3])C=CC=CC=1.C([Sn](Cl)(Cl)CCCC)CCC>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:17][CH2:16][CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:26])=[O:4]

参加物

6

反応物 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 24727429Ethyl 5-cyclohexyl-5-oxovalerate

生成物 1

HCID 666847433-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-thiophene-2-carboxylic acid methyl ester収率 57.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

A flask was charged with 3-amino-thiophene-2-carboxylic acid methyl ester (600 mg, 3.82 mmol, 1.0 equiv), 5-cyclohexyl-5-oxo-pentanoic acid ethyl ester (864 mg, 3.82 mmol, 1.0 equiv), phenyl silane (496 mg, 4.58 mmol, 1.2 equiv), dibutyltin dichloride (116 mg, 0.38 mmol, 0.1 equiv) and dioxane (3.0 mL). The resulting solution was heated at 60° C. for 18 hours. The solution was then concentrated and the residue was purified by silica gel column chromatography, CH2Cl2/heptane 30% to 100%, to give 3-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-thiophene-2-carboxylic acid methyl ester 810 mg (yield 57%).

後処理

  1. concentrationThe solution was then concentrated
  2. customthe residue was purified by silica gel column chromatography, CH2Cl2/heptane 30% to 100%

出典と根拠

ORDレコード
ord-914684d1c8fa49dbb645010e8de4bd36
出典データセット
uspto-grants-2015_05
特許番号
US09040690B2

反応ノート

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