Methyl triflate → (R)-1-(N-(4-methoxy-4-oxo-1-(trimethylammonio)butan-2-yl)sulfamoyl)-3-methyl-1H-imidazol-3-ium chloride trifluoromethanesulfonate

HRID 1958724Notes

Reaction equation

HRID 1958724 reaction equation
[Cl-:1].[N:2]1([S:7]([NH:10][C@H:11]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:12][N+:13]([CH3:16])([CH3:15])[CH3:14])(=[O:9])=[O:8])[CH:6]=[CH:5][N:4]=[CH:3]1.[O:22](C)[S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24]>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[S:23]([O-:25])(=[O:24])=[O:22].[Cl-:1].[CH3:21][O:20][C:18](=[O:19])[CH2:17][C@@H:11]([NH:10][S:7]([N:2]1[CH:6]=[CH:5][N+:4]([CH3:26])=[CH:3]1)(=[O:9])=[O:8])[CH2:12][N+:13]([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 68743870(R)-2-(1H-imidazole-1-sulfonamido)-4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium chloride

Product 1

HCID 86641221(R)-1-(N-(4-methoxy-4-oxo-1-(trimethylammonio)butan-2-yl)sulfamoyl)-3-methyl-1H-imidazol-3-ium chloride trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-2-(1H-imidazole-1-sulfonamido)-4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium chloride in DCM (5 mL), cooled at 0° C., is added methyl triflate (1.05 equiv). After being stirring for 2 h at 0° C., the reaction mixture is concentrated under reduced pressure to give the title compound.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5cb816ebd8884cad9745f01d4a5d8b7f
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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