Water → HCID 23091916, Verbindung

HRID 1393670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1393670
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].O>CN(C)C=O>[C:27]([O:26][C:24]([CH2:23][N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 10264164Benzyl 1H-indole-5-carboxylate

Produkt 1

HCID 23091916HCID 23091916, VerbindungAusbeute 108,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (115 mg) was added to a solution of benzyl 1H-indole-5-carboxylate (600 mg) in N,N-dimethylformamide (2 ml) with ice cooling, and the mixture was stirred for 30 minutes. t-Butyl bromoacetate (562 mg) was added thereto and stirred for 2 hours. Water was added thereto, and the aqueous phase was neutralized and then extracted with dichloromethane. The organic phase was dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give benzyl 1-t-butoxycarbonylmethyl-1H-indole-5-carboxylate (944 mg, Y.: quant.).

Aufarbeitung

  1. stirringstirred for 2 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate anhydrous
  4. concentrationThe product was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f37302ed010d45e18015fa3cb986e1c8
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345180B2

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