Methyl fluorosulfate → (2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1-ethyl-1-methylpyrrolidinium fluorosulfonate

HRID 1030158Notes

Reaction equation

HRID 1030158 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

Reactant 2

HCID 9870Methyl fluorosulfateHCID 14796650(2S, 4S)-2-Carbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

Product 1

HCID 86745657(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1-ethyl-1-methylpyrrolidinium fluorosulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  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

Sources & evidence

ORD record
ord-5d6894ff07ee42259768a1f0575c987a
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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