4-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester → 4-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

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Reaction Steps

4-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester (14.4 g, 40 mmol) was dissolved in 100 mL of tetrahydrofuran containing 10 g of Raney Nickel. The reaction was pressurized with 100 psi of hydrogen gas and stirred for 28 hours at 25° C. to 60° C. The reaction was filtered, and the filtrate was rotary evaporated to give a thick oil. Chromatography (20% ethyl acetate/hexanes, SiO2) of the oil gave 12.2 (92%) of 4-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester as a clear oil. 1H-NMR (CDCl3); δ 7.85 (d, 2H), 7.70 (dd, 1H), 7.27 (m, 3H), 6.78 (m, 2H), 5.18 (bt, 1H), 4.82 (bs, 2H), 4.08 (d, 2H), and 1.57 (s, 9H). MS: M+=363.1 Da Step (3): Synthesis of 4-[(2-Amino-5-bromo-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

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