Hydrochloric Acid → (2S, 4S)-4-(4-Methoxybenzylthio)-2-methoxycarbonylpyrrolidine

HRID 5083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 5083
Cl.C(OC([N:9]1[CH2:13][C@@H:12]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:11][C@H:10]1[C:24]([O:26][CH3:27])=[O:25])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][S:14][C@@H:12]2[CH2:13][NH:9][C@H:10]([C:24]([O:26][CH3:27])=[O:25])[CH2:11]2)=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86745654(2S, 4S)-1-(t-butoxycarbonyl)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine

Produkt 1

HCID 15200411(2S, 4S)-4-(4-Methoxybenzylthio)-2-methoxycarbonylpyrrolidineAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

27.3 ml of a 4N ethyl acetate solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 5.22 g of (2S, 4S)-1-(t-butoxycarbonyl)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine [prepared as described in step (8) above] dissolved in 14 ml of ethyl acetate, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 3.3 g of the title compound as an oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6acb4cb55a2a48bf83975baefbb5272b
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242914

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