Sodium Chloride → (2S, 4S)-1-Ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

HRID 1030165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030165
[CH2:1](I)[CH3:2].C(=O)(O)[O-].[Na+].[CH3:9][O:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][S:16][C@@H:17]2[CH2:21][NH:20][C@H:19]([C:22](=[O:25])[NH:23][CH3:24])[CH2:18]2)=[CH:13][CH:12]=1.[Cl-].[Na+]>CN(C)C=O>[CH2:1]([N:20]1[CH2:21][C@@H:17]([S:16][CH2:15][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:27][CH:26]=2)[CH2:18][C@H:19]1[C:22](=[O:25])[NH:23][CH3:24])[CH3:2]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 14880277(2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Produkt 1

HCID 57039848(2S, 4S)-1-Ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.71 ml of ethyl iodide and 742 mg of sodium bicarbonate were added to a solution of 2.25 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 20 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 1 hour and then at room temperature for 5 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluted with ethyl acetate), to afford 1.87 g of the title compound as colorless crystals, melting at 68°-70° C.

Aufarbeitung

  1. waitat room temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography (eluted with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-729eacf17ca943dca9a19b80d80d8693
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104867

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