Sodium Acetate → 1-BOC-5-acetoxymethyl-7-nitro-indole-2-carboxylic acid methyl ester

HRID 1045844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045844
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14]Br)=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])=[O:4].[C:26]([O-:29])(=[O:28])[CH3:27].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][O:29][C:26](=[O:28])[CH3:27])=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])=[O:4]

Komponenten

4

Edukt 2

HCID 517045Sodium AcetateHCID 594480901-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester

Produkt 1

HCID 594480931-BOC-5-acetoxymethyl-7-nitro-indole-2-carboxylic acid methyl esterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester (10.0 g, 24.2 mmol) prepared in Step B of Preparation 37 was dissolved in N,N-dimethylformamide (50 mL). Sodium acetate (2.4 g, 29.0 mmol) was added thereto, and the mixture was stirred for 4 h at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was purified by column chromatography to give the title compound (4.7 g, Yield 50%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-01ed011a19414e258125fe276b85a8a6
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569307B2

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