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本文在制得青霉素 G亚砜的基础上 ,完成了重排酸的扩环反应 ,重点探讨了扩环反应的最优化条件。青霉素 G亚砜与 N,N′-双 (三甲基甲硅基 )脲 (BSU)在 5 5℃下反应 ,得到亚砜的酯化物。加入催化剂吡啶乙酰溴 ,回流条件下发生扩环反应。最后加水脱去酯基 ,加酸析出产物重排酸。通过正交实验可得出以下结论 :当 N,N′-双 (三甲基甲硅基 )脲 -亚砜为 2 .5 :1,乙酰溴 -亚砜为 0 .4:1,吡啶 -乙酰溴为 1.5 :1,回流时间为 3.5 h,酸化 p H值为 1.8时 ,扩环反应结果最好 ,总收率可达 76 % ,纯度 97%以上。
In this paper, based on the preparation of penicillin G sulfoxide, the completion of the rearrangement acid ring expansion reaction, focusing on the expansion ring reaction optimization conditions. Penicillin G sulfoxide was reacted with N, N’-bis (trimethylsilyl) urea (BSU) at 5 ° C to give the sulfoxide esterified product. Pyridine acetyl bromide catalyst was added, the expansion ring under reflux conditions. Finally, add water to remove the ester group, add acid precipitation product rearrangement acid. Orthogonal experiments can be concluded as follows: when N, N’-bis (trimethylsilyl) urea-sulfoxide is 2.5: 1, acetyl bromide-sulfoxide is 0.4: 1, Acetyl bromide was 1.5: 1, reflux time was 3.5 h, and the acid value of p H was 1.8. The result of ring expansion was the best. The total yield was up to 76% and the purity was above 97%.