Methyl iodide → 3-(Methyl-pent-4-enyl-sulfamoyl)-propionic acid methyl ester

HRID 1432126Notes

Reaction equation

HRID 1432126 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][S:6](=[O:14])(=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].[C:16]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][S:6](=[O:14])(=[O:13])[N:7]([CH3:16])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 860520453-Pent-4-enylsulfamoyl-propionic acid methyl ester

Product 1

HCID 860520473-(Methyl-pent-4-enyl-sulfamoyl)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 1.03 g (12.0 mmol) pent-4-enylamine, 8 ml DCM and 5 ml 10% aqueous Na2CO3 at 0° C. are added dropwise 2.25 g (12.0 mmol) 3-chlorosulfonyl-propionic acid methyl ester. After stirring for 2 h at 25° C. the phases are separated and the organic phase is dried with sodium sulfate and evaporated. Chromatography on silica gel (EtOAc, hexane 1:2) gives the 3-pent-4-enylsulfamoyl-propionic acid methyl ester. This ester is dissolved in 2 ml DMF and heated to 65° C. in the presence of 1.58 g (11.5 mmol) K2CO3 and 0.716 ml methyl iodide for 5 h. The mixture is diluted with EtOAc and washed with water, dried with sodium sulfate and evaporated. Chromatography on silica gel (EtOAc, hexane 1:4) gives the 3-(methyl-pent-4-enyl-sulfamoyl)-propionic acid methyl ester. Hydrolysis of this ester with LiOH in water/MeOH gives the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-d825db75a4194f1da573228081fe8325
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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