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

HRID 1030166Notes

Reaction equation

HRID 1030166 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-methylcarbamoyl-pyrrolidine 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-de1dc3ec9f684f83840851881221fc86
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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