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

HRID 579186노트

반응식

HRID 579186 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
60 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-914684d1c8fa49dbb645010e8de4bd36
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040690B2

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