Methanesulfonyl chloride → n-(4-Methanesulfonylamino-2-sulfamoylphenyl)malonamic acid methyl ester

Participants

Reaction Steps

In the new route the order of the function group incorporation for the last 3 steps is changed. The first intermediate, 2-amino-5-nitrobenzenesulfonamide (II) is common to both routes. This intermediate is treated with methyl 3-chloro-3-oxopropanoate in acetonitrile. The nitro group is then reduced using hydrogen and palladium on carbon catalyst in a mixture of THF/DMF. Finally mesylation in acetonitrile using methanesulfonyl chloride and pyridine as the base provides the key intermediate N-(4-methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid methyl ester (V).

Provenance & Evidence