Ethanol → ethyl 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionate

HRID 274047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274047
S(Cl)(Cl)=O.[CH2:5]([NH:12][CH:13]1[CH2:19][C:18]2[CH:20]=[C:21]([O:24][C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=[O:27])[CH:22]=[CH:23][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+].[CH2:36](O)[CH3:37]>>[CH2:5]([NH:12][CH:13]1[CH2:19][C:18]2[CH:20]=[C:21]([O:24][C:25]([CH3:30])([CH3:29])[C:26]([O:28][CH2:36][CH3:37])=[O:27])[CH:22]=[CH:23][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 200947372-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionic acid

Produkt 1

HCID 20094801ethyl 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionate

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Thionyl chloride (0.2 ml) was added dropwise to ethanol (5 ml) with stirring at -10° C. After stirring for ten minutes, 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionic acid (0.49 g) was added portionwise to the mixture. The reaction mixture was stirred at ambient temperature for 1 hour and then refluxed for 3 hours. After cooling, the mixture was poured into an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with chloroform-methanol (100:1) to give ethyl 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionate (0.43 g).

Aufarbeitung

  1. stirringAfter stirring for ten minutes
  2. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  3. temperaturerefluxed for 3 hours
  4. temperatureAfter cooling
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel with chloroform-methanol (100:1)

Quellen und Nachweise

ORD-Eintrag
ord-6ebccb6c61f34640b1a0fd1246edf423
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387710

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