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

HRID 5105

Reaction equation

HRID 5105 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

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-429411c0a3c042dbbf0eb9f928ca4f75
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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