Synthesis And Characterization Of (S)-N-(2-benzy-loxy-propenyl)-t-butyl Carbazate

Pharmaceutical intermediate (S)-N-(2-benzyloxy-propenyl)-t-butyl carbazate is animportant pharmaceutical polymer raw material. it’s used for oxamic hydrazide and someagents antiphlogistic. The synthesis methods of (S)-N-(2-benzyloxy-propenyl)-t-butylcarbazate reported in the literature had many shortcomings,such as high raw material costs,low production yield, not suitable for mass production and so on. In order to solve theproblems, this paper studied a new synthetic route.(S)-2-benzyloxy propanal wassynthesized by the amination reaction of the pyrrolidine, sodium hydride and benzyl chloridein the etherification reaction, the red aluminum reduction reaction with (S)-ethyl lactate asraw material,(S)-N-(2-benzyloxy-propenyl)-t-butyl was synthesized by oximation reactionoft-butyl carazate with the (S)-2-benzyloxy propanal as raw material.(S)-2-benzyloxyl propanal was synthesized by amination of pyrrolidine, etherification ofbenzyl chlorine and Sodium bisaluminiumhydride with Erhyl (S)-lactate as raw material. Thereaction time, the reaction temperature and the mole ratio of raw material were investigated inthe process of amination. The results showed that the yield of amination reaction was about94%when amination reaction time was72h, the reaction temperature was25℃and the moleratio of pyrrolidine to Erhyl (S)-lactate is1.4∶1, The overall yield was about61.8%. Theproduct structure was characterized by GC-MS、IR or1H-NMR.T-butyl carbazate was synthesized by esterification of tert-butatol and hydrazinolysis ofhydrazine hydrate with phenyl chloroformate as raw material. The various factors of affectingthe reaction in the process of esterification and hydrazine were investigated. The resultsshowed that under the conditions of esterification reaction time is3h and the reactiontemperature is25~30℃, the yield of t-butyl phenyl carbonate is about77%;when the moleratio of hydrazine hydrate to t-butyl phenyl carbonate is2:1, the reaction temperature is100℃,the yield of t-butyl carbazate is up to93%.The overall yield is about72%. The productstructure was characterized by GC-MS、IR or1H-NMR.(S)-N-(2-benzyloxy-propenyl)-t-butyl carbazate was synthesized with (S)-2-benzyloxylpropanal and T-butyl carbazate by oximation reaction at room temperature, the total yield is56%, The product structure was characterized by GC-MS、IR or1H-NMR, for after further research provides the theoretical basis.