Potassium Carbonate → ethyl 3-[N,N'-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylate

HRID 557472

Reaktionsgleichung

Reaktionsgleichung von HRID 557472
[O:1]=[C:2]1[CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][C:4](=[O:12])[NH:3]1.[N:13]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[N:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH2:28]([O:27][C:25]([N:13]([C:6]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][C:4](=[O:12])[NH:3][C:2]1=[O:1])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 23635561Ethyl 2,5-dioxo-3-pyrrolidinecarboxylate

Produkt 1

HCID 58382718ethyl 3-[N,N'-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2,5-dioxopyrrolidine-3-carboxylate (3.92 g) in ethyl acetate (60 ml) was added dibenzyl azodicarboxylate (7.27 g), followed by potassium carbonate (317 mg) at room temperature. After this mixture was stirred at room temperature for 1 hour, the mixture was filtered through a Celite pad. The filtrate was concentrated and the resulting residue was purified by a flash column chromatography (hexane:ethyl acetate=2:1) to give the ethyl 3-[N,N′-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylate (10.1 g, 94%) as amorphous.

Aufarbeitung

  1. filtrationthe mixture was filtered through a Celite pad
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified by a flash column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-4faacf44633047b4ade76eefc09a49e6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058456B2

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