Methyl iodide → N-[4-methoxybenzenesulfonyl]-(D)-asparagine methyl ester

HRID 264324

Reaktionsgleichung

Reaktionsgleichung von HRID 264324
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@@H:13]([C:18]([OH:20])=[O:19])[CH2:14][C:15](=[O:17])[NH2:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:21](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.[Cl-].[NH4+]>[CH3:21][O:19][C:18](=[O:20])[C@@H:13]([CH2:14][C:15](=[O:17])[NH2:16])[NH:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27014145N-[4-methoxybenzenesulfonyl]-(D)-asparagine

Produkt 1

HCID 70060643N-[4-methoxybenzenesulfonyl]-(D)-asparagine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

N-[4-methoxybenzenesulfonyl]-(D)-asparagine (10.1 g, 33.3 mmol) is dissolved in dimethylformamide (167.0 mL). Cesium carbonate (5.43 g, 16.66 mmol) is added, followed by the addition of methyl iodide (2.22 mL, 33.3 mmol), and the reaction is stirred overnight. The reaction is then diluted with saturated ammonium chloride (366.0 mL), and extracted well with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is recrystallized from toluene to provide N-[4-methoxybenzenesulfonyl]-(D)-asparagine methyl ester.

Aufarbeitung

  1. extractionextracted well with ethyl acetate
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe crude product is recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-c55e599db2fe4a409d14e14afe953590
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646167

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