反应 #51154

反应方程式

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

hydrogen

→

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

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   过滤The reaction was filtered
2. 2
   其他the filtrate was rotary evaporated
3. 3
   其他to give a thick oil

实验过程

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

来源