Methyl fluorosulfate → HCID 10812348, compound

HRID 1030135Notes

Reaction equation

HRID 1030135 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][F: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][F:27])[CH3:6])(=[O:9])[NH2:8]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 10781417(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1-(2-fluoroethyl)pyrrolidine

Product 1

HCID 10812348HCID 10812348, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.17 ml of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 630 mg of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-(2-fluoroethyl)-pyrrolidine [prepared as described in step (1) above] dissolved in 12 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 pressure to afford 850 mg of the title compound as an oil.

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 under reduced pressure

Sources & evidence

ORD record
ord-61c4635e3c604301a674b2bdff00a0c0
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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