Methyl fluorosulfate → (2S, 4S)-1-Ethyl-1-methyl-2-methylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

HRID 5105

Reaktionsgleichung

Reaktionsgleichung von HRID 5105
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[CH2:7]([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:27])[NH:25][CH3:26])[CH3:8]>C(Cl)Cl>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[CH2:7]([N+:9]1([CH3:6])[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:27])[NH:25][CH3:26])[CH3:8]

Komponenten

4

Edukt 2

HCID 9870Methyl fluorosulfateHCID 57039848(2S, 4S)-1-Ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Produkt 1

HCID 86745659(2S, 4S)-1-Ethyl-1-methyl-2-methylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

187 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 700 mg of (2S, 4S)-1-ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 30 ml of dry methylene chloride, and the mixture was stirred at room temperature for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed repeatedly by decantation with diethyl ether and dried under reduced pressure to afford 950 mg of the title compound as a colorless oil.

Aufarbeitung

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. washthe residue was washed repeatedly by decantation with diethyl ether
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-429411c0a3c042dbbf0eb9f928ca4f75
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242914

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