Arcyriarubin A → HCID 18780301, Verbindung

HRID 345673

Reaktionsgleichung

Reaktionsgleichung von HRID 345673
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:13](=[O:27])[NH:14][C:15](=[O:26])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[CH:4]1.C[Si](Cl)(C)C.[CH2:33]1[O:36][CH:34]1[CH3:35]>CN(C=O)C.O>[OH:36][CH:34]([CH3:33])[CH2:35][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:13](=[O:27])[NH:14][C:15](=[O:26])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:33][CH:34]([OH:36])[CH3:35])[CH:18]=2)=[CH:4]1

Komponenten

7

Edukt 4

HCID 2399Arcyriarubin AHCID 6378Propylene OxideHCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydride2×

Produkt 1

HCID 18780301HCID 18780301, VerbindungAusbeute 6,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

40 mg of a 60% suspension of sodium hydride in mineral oil was added to a solution of 327 mg of 3,4-bis-(3-indolyl)-1H-pyrrole-2,5-dione in 5 ml of DMF at 0° C. under nitrogen. After 0.5 hour the mixture was cooled to -20° C. and 108 mg of trimethylsilyl chloride were added. The mixture was allowed to warm to room temperature, then cooled to 0° C. and then a further 80 mg of sodium hydride were added thereto. After 0.5 hour at 0° C. 116 mg of propylene oxide were added and the mixture was stirred overnight. 5 ml of water were added and the mixture was extracted with dichloromethane. The organic phase was dried and evaporated. The residue was purified on silica gel with ethyl acetate/petroleum ether. Recrystallization from diethyl ether/petroleum ether gave 30 mg of 3,4-bis[1-(2-hydroxypropyl)-3-indolyl]-1H-pyrrole-2,5-dione, m.p. 133°-135° C.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. temperaturecooled to 0° C.
  3. extractionthe mixture was extracted with dichloromethane
  4. customThe organic phase was dried
  5. customevaporated
  6. customThe residue was purified on silica gel with ethyl acetate/petroleum ether
  7. customRecrystallization from diethyl ether/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-85b5792b3e8b4a12a24c72c9339ed02d
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057614

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