Process for producing optically active benzene-sulfonamide...

Details Process for producing optically active benzene-sulfonamide... Process for producing optically active benzene-sulfonamide...

C - Chemistry, Metallurgy

07

C

260/542.5

C07C 311/37 (2006.01) C07C 303/40 (2006.01) C07C 311/15 (2006.01)

Patent

CA 1340332

The present invention is directed to processes for producing optically active benzenesulfonamide derivatives useful as antihypotension agents and intermediates of optically active drugs. The optically active benzenesulfonamide derivates are represented by the general formula (I) (see fig. I) (wherein R1 and R2 are same or different hydrogen atom or a lower alkyl group; R3 denotes hydrogen atom, a lower alkyl, hydroxyl or a lower alkoxyl group; and R4 stands for a lower alkyl group). The processes comprise either decomposing a m-(2-substituted- alkylaminoalkyl)benzenesulfonamide derivative represented by the general formula (II) (see fig. II) (wherein R1, R2, R3 and R4 are as defined above; R5 denotes a lower alkyl, carboxy-lower-alkyl or a lower-alkoxycarbonyl-lower-alkyl group; and R6 is a substituted or unsubstituted phenyl, carboxyl or a lower-alkoxycarbonyl group), or reacting a sulfamoyl-substituted benzyl lower ketone represented by the general formula (III) (see fig. III) (wherein R1, R2, R3 and R4 are as defined above) with an optically active, substituted alkylamine represented by the general formula (IV) (see fig. IV) (wherein R5 denotes a lower alkyl, a carboxy-lower-alkyl or a lower-alkoxycarbonyl-lower-alkyl group; and R6 is a substituted or unsubstituted phenyl, carboxyl or a lower-alkoxycarbonyl group) in the presence of a reducing agent to form a m-(2-substituted- alkylaminoalkyl)benzenesulfonamide derivative represented by the general formula (II) (see fig. V) (wherein R1, R2, R3, R4, R5 and R6 are as defined above), and decomposing the substituted alkylamino derivative thus formed.

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