青霉素G亚砜对甲氧基苄酯的合成研究

Study on Synthesis of P-methoxybenzyl Penicillin G Sulfoxide Ester

目的:合成青霉素G亚砜对甲氧基苄酯(化合物A)。方法:以青霉素G钾盐和对甲氧基苄氯(1.1∶1)为原料,四丁基溴化铵(TBAB)为催化剂,三氯甲烷/N,N-二甲基甲酰胺(DMF)为溶剂,过氧乙酸为氧化剂合成化合物A,并进行核磁共振结构表征。以收率为指标,确定较佳的酯化反应温度、酯化反应时间、TBAB用量等反应条件。结果:制备得到了化合物A(收率88%,纯度98.5%)并经过结构表征证实。化合物A的最佳反应条件是酯化反应温度为50℃,酯化反应时间为4h,TBAB用量为0.5%。结论:以确定的反应条件可得到目标化合物,合成周期短,利于工业化生产。

OBJECTIVE： To synthesize P-methoxybenzyl penicillin G sulfoxide ester （compound A）. METHODS： Compound A was synthesized by using potassium penicillin G and P-methoxybenzyl （1.1 ： 1 ） as raw material, tetrabutyl ammonium bromide （TBAB） as catalytic agent, trichloromethane/N, N-dimethylformamide as solvent and peroxyacetic acid as oxidation agent; the structure of it was characterized by NMR. The optimal reaction conditions such as reaction temperature, reaction time, amount of TBAB were well studied with yield as index. RESULTS： Compound A （yield of 88%, purity of 98.5% ） were obtained and confirmed. The optimal reaction condition of compound A was as follows： esterification temperature of 50 ℃, esterification time of 4 h, TBAB amount of 0.5%. CONCLUSIONS： Target compound could be obtained by this technology. The synthetic cycle is short, which is suitable for industrial production.