4-Chlorobenzenesulfonyl chloride → HCID 14986647, compound

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Reaction Steps

The above compound (4 g) is dissolved in 75 mL of methanol saturated with ammonia gas, activated Raney Nickel is added and the mixture hydrogenated in an atmosphere of hydrogen at 3 atmospheres pressure for 20 hours. The catalyst is filtered off and the methanol solution evaporated to give a residue which is taken up in ethyl acetate. The solution of the resulting amine is treated with 5 mL of triethylamine and 3 g of 4-chlorobenzenesulfonyl chloride. The reaction mixture is evaporated to give a residue which is purified by chromatography over silica gel using a mixture of ether/hexane (7:3) as eluent to yield ethyl 7-(3-pyridyl)-2-ethoxycarbonyl-2-[6-(p-chloro- phenylsulfonamido)-hexyl]-heptanoate, also named ethyl 8-(p-chlorophenylsulfonamido)-2-[5-(3-pyridyl)-pentyl]-2-(ethoxycarbonyl)-octanoate.

Provenance & Evidence