Hydrochloric Acid → (2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

HRID 5101

Reaktionsgleichung

Reaktionsgleichung von HRID 5101
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:28])[NH:25][CH2:26][CH3:27])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:26]([NH:25][C:24]([C@@H:10]1[CH2:11][C@H:12]([S:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH2:13][NH:9]1)=[O:28])[CH3:27]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14880290(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

Produkt 1

HCID 14880286(2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidineAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

41.19 ml of a 4N ethyl acetate solution of hydrogen chloride were added to a solution of 13.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 100 ml of ethyl acetate, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The aqueous layer was saturated with ammonium chloride and extracted with tetrahydrofuran. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through silica gel (eluted with a 87:13 by volume mixture of ethyl acetate and methanol) to afford 8.00 g of the title compound as pale brown crystals, melting at 67°-68° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionextracted with tetrahydrofuran
  3. washThe combined extracts were washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. washeluted with a 87:13 by volume mixture of ethyl acetate and methanol)

Quellen und Nachweise

ORD-Eintrag
ord-b7a72d018267442bb83530e1ef42bd9e
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242914

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