Methyl fluorosulfate → (2S, 4S)-2-Ethylcarbamoyl-1-ethyl-1-methyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

HRID 1030164Notes

Reaction equation

HRID 1030164 reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[CH2:7]([NH:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14][N:13]1[CH2:27][CH3:28])=[O:11])[CH3:8]>C(Cl)Cl>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[CH2:7]([NH:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:14][N+:13]1([CH2:27][CH3:28])[CH3:6])=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 14880288(2S, 4S)-2-Ethylcarbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

Product 1

HCID 86745658(2S, 4S)-2-Ethylcarbamoyl-1-ethyl-1-methyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

233 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 910 mg of (2S, 4S)-2-ethylcarbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 35 ml of dry methylene chloride, and the mixture was stirred at room temperature for 3.5 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 1.20 g of the title compound as a pale brown 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-7cc3fa0c7a7c4919afaa56b725ccc79a
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

Loading…