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

HRID 579186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579186
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 666847433-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-thiophene-2-carboxylic acid methyl esterAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-914684d1c8fa49dbb645010e8de4bd36
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040690B2

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