Amino-2-hydroxy-4-phenylbutanoic acid(compound 3), the key intermediate for the synthesis of Bestatin, was prepared via substitution, condensation and reduction in an overall yield of about 47.8%. The reaction of nitr...Amino-2-hydroxy-4-phenylbutanoic acid(compound 3), the key intermediate for the synthesis of Bestatin, was prepared via substitution, condensation and reduction in an overall yield of about 47.8%. The reaction of nitromethane with benzyl bromide in the presence of sodium ethoxide gave a 82% yield of 1-nitro-2-phenylethane(compound 1). The condensation of compound 1 with glyoxylic acid monohydrate in sodium ethoxide/ethanol afforded a 72% yield of 3-nitro-2-hydroxy-4-phenylbutyric acid(compound 2), which was hydrogenated to compound 3 with a 81% yield in acetic acid in the presence of Pd/C. All the compounds were characterized by 1H NMR, IR and elemental analysis.展开更多
苯基吡拉西坦是一类新型促智药。以4-氨基-3-苯基丁酸盐酸盐为原料与甲醇发生酯化反应、然后在三乙胺作用下发生氨解环合反应,合成中间体4-苯基-2-吡咯烷酮(1)。在氢化钠存在下,4-苯基-2-吡咯烷酮与溴乙酸乙酯发生烷基化反应,生成2-氧代...苯基吡拉西坦是一类新型促智药。以4-氨基-3-苯基丁酸盐酸盐为原料与甲醇发生酯化反应、然后在三乙胺作用下发生氨解环合反应,合成中间体4-苯基-2-吡咯烷酮(1)。在氢化钠存在下,4-苯基-2-吡咯烷酮与溴乙酸乙酯发生烷基化反应,生成2-氧代-4-苯基-1-吡咯烷乙酸乙酯(2)。然后在室温下与氨水再次经氨解得到目标产物苯基吡拉西坦(3)。将4-苯基-2-吡咯烷酮的合成路线缩短为一步反应。总体反应路线步骤短,条件温和,对设备要求不苛刻,适合工业化生产。目标产物及中间体经1 H NMR和IR表征。展开更多
文摘Amino-2-hydroxy-4-phenylbutanoic acid(compound 3), the key intermediate for the synthesis of Bestatin, was prepared via substitution, condensation and reduction in an overall yield of about 47.8%. The reaction of nitromethane with benzyl bromide in the presence of sodium ethoxide gave a 82% yield of 1-nitro-2-phenylethane(compound 1). The condensation of compound 1 with glyoxylic acid monohydrate in sodium ethoxide/ethanol afforded a 72% yield of 3-nitro-2-hydroxy-4-phenylbutyric acid(compound 2), which was hydrogenated to compound 3 with a 81% yield in acetic acid in the presence of Pd/C. All the compounds were characterized by 1H NMR, IR and elemental analysis.
文摘苯基吡拉西坦是一类新型促智药。以4-氨基-3-苯基丁酸盐酸盐为原料与甲醇发生酯化反应、然后在三乙胺作用下发生氨解环合反应,合成中间体4-苯基-2-吡咯烷酮(1)。在氢化钠存在下,4-苯基-2-吡咯烷酮与溴乙酸乙酯发生烷基化反应,生成2-氧代-4-苯基-1-吡咯烷乙酸乙酯(2)。然后在室温下与氨水再次经氨解得到目标产物苯基吡拉西坦(3)。将4-苯基-2-吡咯烷酮的合成路线缩短为一步反应。总体反应路线步骤短,条件温和,对设备要求不苛刻,适合工业化生产。目标产物及中间体经1 H NMR和IR表征。
