Dibutyltin dichloride → 3-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 579190ノート

反応式

HRID 579190 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[CH2:17]([O:19][C:20](=[O:32])[CH2:21][CH2:22][CH2:23][C:24]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=O)[CH3:18].C1([SiH3])C=CC=CC=1.C([Sn](Cl)(Cl)CCCC)CCC>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:24]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:23][CH2:22][CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:32])=[O:4]

参加物

6

反応物 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylateHCID 24727429Ethyl 5-cyclohexyl-5-oxovalerate

生成物 1

HCID 666847743-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester収率 15.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

A flask was charged with 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (515 mg, 2.2 mmol, 1.0 equiv), 5-cyclohexyl-5-oxo-pentanoic acid ethyl ester (500 mg, 2.2 mmol, 1.0 equiv), phenyl silane (240 mg, 2.2 mmol, 1.0 equiv), dibutyltin dichloride (67 mg, 0.22 mmol, 0.1 equiv) and dioxane (2.0 mL). The resulting solution was heated at 120° C. with microwave for 2 hours. The solution was then concentrated and the residue was purified by silica gel column chromatography, EtOAc/heptane 5% to 40%, to give oil that contained starting material. The material was further purified with silica gel column chromotography, EtOH/DCM 2% to 10% to give product 150 mg (yield 15%).

後処理

  1. concentrationThe solution was then concentrated
  2. customthe residue was purified by silica gel column chromatography, EtOAc/heptane 5% to 40%
  3. customto give oil that
  4. customThe material was further purified with silica gel column chromotography, EtOH/DCM 2% to 10%

出典と根拠

ORDレコード
ord-913d4c4d0c9443fa82c38552d7f49b8d
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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