Sodium hydride → N-(5-nitro-2-(pyrrol-1-yl)phenylmethyl)iminodicarboxylic acid di-tert-butyl ester

HRID 2227471

Reaktionsgleichung

Reaktionsgleichung von HRID 2227471
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:9])([CH3:6])([CH3:5])[CH3:4].[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH:33]=[CH:32][CH:31]=[CH:30]2)=[C:25]([CH:28]=1)[CH2:26]Br)([O-:20])=[O:19]>CN(C)C=O>[C:14]([O:13][C:11]([N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:26][C:25]1[CH:28]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=[CH:23][C:24]=1[N:29]1[CH:33]=[CH:32][CH:31]=[CH:30]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 184740025-Nitro-2-(pyrrol-1-yl)benzyl bromide

Produkt 1

HCID 54574337N-(5-nitro-2-(pyrrol-1-yl)phenylmethyl)iminodicarboxylic acid di-tert-butyl esterAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a mixture of sodium hydride (60% content, 21 mg), iminodicarboxylic acid di-tert-butyl ester (117 mg) and dimethylformamide (5 ml), a solution in dimethylformamide (3 ml) of the compound (137 mg) obtained in Example 1c was added dropwise under cooling with ice. The reaction mixture was stirred for 2 hours at room temperature and then concentrated at reduced pressure. Brine was added to the resulting residue and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9) to give the titled compound (yield, 74%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. concentrationconcentrated at reduced pressure
  3. additionBrine was added to the resulting residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-19e89b8f35bd47a78da4095de7164f59
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06414005B1

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