Methyl fluorosulfate → (2S, 4S)-1,1-Dimethyl-2-methylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfate

HRID 5076

Reaction equation

HRID 5076 reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[CH3:7][O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][S:14][C@@H:15]2[CH2:19][N:18]([CH3:20])[C@H:17]([C:21](=[O:24])[NH:22][CH3:23])[CH2:16]2)=[CH:11][CH:10]=1>C(Cl)Cl>[S:2]([F:1])([O-:5])(=[O:4])=[O:3].[CH3:20][N+:18]1([CH3:6])[CH2:19][C@@H:15]([S:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:26][CH:25]=2)[CH2:16][C@H:17]1[C:21](=[O:24])[NH:22][CH3:23]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 14880279(2S, 4S)-4-(4-Methoxybenzylthio)-1-methyl-2-methylcarbamoylpyrrolidine

Product 1

HCID 86747188(2S, 4S)-1,1-Dimethyl-2-methylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

280 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 210 mg of (2S, 4S)-4-(4-methoxybenzylthio)-1-methyl-2-methylcarbamoylpyrrolidine [prepared as described in step (5) above] dissolved in 30 ml of dry methylene chloride. The mixture was stirred at the same temperature for 30 minutes and then at room temperature for 5 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 rpessure, to afford 281 mg of the title compound as a colorless powder.

Workup

  1. waitat room temperature for 5 hours
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. washthe residue was washed repeatedly by decantation with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-1d2785f1e38445e281416d2d2b06b4b3
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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