Benzenesulfonyl chloride → Methyl beta-[3-(cyano)phenyl]-4-[(phenylsulfonyl)amino]benzenepentanoate

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Reaction Steps

Part A. methyl 3-(3-cyanophenyl)-5-(4-aminophenyl)pentanoate (0.100 gm, 0.325 mmol) was dissolved in dioxane and 0.5 mL of 1 N NaOH was added, followed by benzenesulfonyl chloride. The solution was stirred for 1 hour, quenched in 1 N HCl and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over MgSO4. The solvent was removed under vacuum and the residue was chromatographed on silica gel eluting ethyl acetate:toluene (20:80, v:v) to give methyl beta-[3-(cyano)phenyl]-4-[(phenylsulfonyl)amino]benzenepentanoate as an oil 0.060 gm (41%). MS: (M+NH4)+ 466; 1H NMR (CDCl3): 1.9 (m, 2H), 2.35 (m, 2H), 2.6 (m, 2H), 3.15 (m, 1H), 3.55 (s, 3H), 6.95 (s, 4H), 7.45 (m, 5H), 7.55 (m, 2H), 7.75 (d, 2H).

Provenance & Evidence