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

HRID 5111Notes

Reaction equation

HRID 5111 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][CH2:26][OH:27])(=[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:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12][N+:11]1([CH2:25][CH2:26][OH:27])[CH3:6])(=[O:9])[NH2:8]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 14796669(2S, 4S)-2-Carbamoyl-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)pyrrolidine

Product 1

HCID 14880303(2S, 4S)-2-Carbamoyl-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidinium fluorosulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.108 ml of methyl fluorosulfonate was added dropwise at room temperature to a solution of 0.38 of (2S, 4S)-2-carbamoyl-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)pyrrolidine dissolved in 7.5 ml of dry methylene chloride, and the mixture was stirred at the same temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed by decantation with diethyl ether and dried under reduced pressure, to afford 0.396 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 by decantation with diethyl ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-c40fc1cfcee0401fbf2b804fba54c690
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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