2-Nitrobenzenesulfonyl chloride → Methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

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Reaction Steps

To a solution of methyl 3-(4-aminophenyl)propanoate (2.69 g, 15.0 mmol) in pyridine (20 mL) was added 2-nitrobenzenesulfonyl chloride (3.99 g, 18.0 mmol) by small portions, and the mixture was stirred at room temperature for 45 hr. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the obtained residue. The mixture was stirred with heating at 80° C. for 15 min and filtrated through celite. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30%-60% ethyl acetate/hexane) to give the title compound (3.39 g, yield 62%) as yellow prism crystals.

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