反应详情

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).

1. customquenched in 1 N HCl
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with water and brine
4. dry with materialdried over MgSO4
5. customThe solvent was removed under vacuum
6. customthe residue was chromatographed on silica gel
7. washeluting ethyl acetate:toluene (20:80, v:v)