Methyl fluorosulfate → (6S, 8S)-1,4-Dimethyl-8-(4-methoxybenzylthio)-5-oxo-4-aza-1-azoniabicyclo[4.3.0]nonane fluorosulfonate

HRID 5117Notes

Reaction equation

HRID 5117 reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[CH3:7][O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][S:14][C@@H:15]2[CH2:23][N:22]3[C@H:17]([C:18](=[O:25])[N:19]([CH3:24])[CH2:20][CH2:21]3)[CH2:16]2)=[CH:11][CH:10]=1>C(Cl)Cl.C(OCC)C>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:6][N+:22]12[CH2:23][C@@H:15]([S:14][CH2:13][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:27][CH:26]=3)[CH2:16][C@H:17]1[C:18](=[O:25])[N:19]([CH3:24])[CH2:20][CH2:21]2

Participants

5

Reactant 2

HCID 9870Methyl fluorosulfateHCID 56999702HCID 56999702, compound

Product 1

HCID 86747190(6S, 8S)-1,4-Dimethyl-8-(4-methoxybenzylthio)-5-oxo-4-aza-1-azoniabicyclo[4.3.0]nonane fluorosulfonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

461 μl of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 1.71 g of (6S, 8S)-8-(4-methoxybenzylthio)-4-methyl-5-oxo-1,4-diazabicyclo-[4.3.0]nonane dissolved in 60 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the mixture was diluted with diethyl ether, and the resulting crystals were collected by filtration and dried under reduced pressure, to afford 2.09 g of the title compound as colorless crystals, melting at 208°-210° C.

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-af6090bbcc8144a0a01582239a197438
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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