Methyl fluorosulfate → (2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1-ethyl-1-methylpyrrolidinium fluorosulfonate
Reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[C:7]([C@@H:10]1[CH2:14][C@H:13]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12][N:11]1[CH2:25][CH3:26])(=[O:9])[NH2:8]>C(Cl)Cl>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[C:7]([C@@H:10]1[CH2:14][C@H:13]([S:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH2:12][N+:11]1([CH2:25][CH3:26])[CH3:6])(=[O:9])[NH2:8]Participants
4
Procedure
0.43 ml of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 1.44 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-ethylpyrrolidine dissolved in 30 ml of dry methylene chloride and the mixture was stirred at room temperature for 2 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 2.0 g of the title compound as an oil.