Sodium Carbonate → HCID 86052045, compound
Reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH:4]=[CH2:5].C([O-])([O-])=O.[Na+].[Na+].[CH3:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][S:18](=[O:20])(=[O:19])[NH:6][CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
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
- customare separated
- dry with materialthe organic phase is dried with sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-239ea6ee8e4047cbbe8f500d389a841c
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612055B2
Reaction notes
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