N-苄氧羰基-L-丝氨酸苄酯的合成研究与改进

Study and Improvement on Synthesis of N-Cbz-L-serine benzyl ester

摘要:

摘要：以苄氧羰基氯、L -丝氨酸为原料，合成了N -苄氧羰基-L-丝氨酸。通过正交实验考察了反应温度、pH、原料的摩尔比、相转移催化剂对N -苄氧羰基-L-丝氨酸收率的影响。优化反应条件后N-苄氧羰基-L-丝氨酸收率为93.2%。N -苄氧羰基-L-丝氨酸和苄溴反应生成了目标产物-N-苄氧羰基-L-丝氨酸苄酯，重点探讨了酯化过程中缚酸剂、原料的投料顺序及产品后处理对目标产物得率的影响。选择具有催化作用的三乙胺为缚酸剂，用10%的亚硫酸氢钠对产品进行后处理使得N-苄氧羰基-L-丝氨酸苄酯的纯度达98.5%。通过红外、核磁、熔点、旋光度等对目标产品进行了结构表征, 用高效液相色谱对产品的纯度进行了测定。

Abstract:

Abstract:Benzyloxycarbonyl chloride(CbzCl), L-serine was used to synthesize N-Cbz-L-serine. Reaction temperature, pH, the molar ratio of the starting materials and phase transfer catalyst was studied by orthogonal experiments. The optimum yield of N-Cbz-L-serine could reach to 93.2%. N-Cbz-L-serine benzyl ester was prepared by reaction of N-Cbz-L-serine and benzyl bromide. The effects of acid-binding agent, the feeding order of the starting materials and after treatment of product were investigated. The final results show that the N-Cbz-L-serine benzyl ester was catalyzed by triethylamine, which also was used as acid-binding agent. The purity of N-Cbz-L-serine benzyl ester can reach 98.5% by treatment of 10% sodium bisulfite. IR, 1HNMR, melting point, optical activity were applied to confirm the structure of the target molecule. HPLC was used to analyze the purity of product.