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

HRID 579190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579190
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 666847743-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-5-phenyl-thiophene-2-carboxylic acid methyl esterAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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%

Quellen und Nachweise

ORD-Eintrag
ord-913d4c4d0c9443fa82c38552d7f49b8d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040690B2

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