Dissertation > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Antibiotics manufacture

The Synthesis of Panipenem-Betamipron

Author WangQiJun
Tutor XuDongCheng
School Zhejiang Normal University
Course Organic Chemistry
Keywords Carbapenem Antibiotic Panipenem Betamipron
Type Master's thesis
Year 2009
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The Panipenem - betamipron Sankyo , Japan in 1983 developed the second carbapenem antibiotic drugs, has a broad spectrum antimicrobial, antibacterial activity . The inverse synthetic Panipenem analysis and design of a viable synthetic route , and success in this route for the synthesis of the target product Panipenem . Panipenem - fold betamipron conducted a synthesis study : Methyl acetoacetate 2 -nitrobenzyl alcohol 3 and the monocyclic β-lactam 18 as raw material , after transesterification , diazotization six step reaction, the completion of a total yield of 48.2% of the 9 Construction panipenem bicyclic nucleus ; ( 3R ) - 3 - hydroxy - pyrrolidine hydrochloride as a starting material , through a four-step reaction , and ultimately to 63.7% the completion of the total yield of the side chain of panipenem 13 Construction ; last the nucleus 9 and the side chain 13 is condensed diphenoxy phosphorus oxychloride and the conditions of diisopropylethylamine docking , and then through the catalytic hydrogenolysis protection and imidization completion of the two-step reaction panipenem build three-step total yield of 43.5% . The entire route of 13 , the total yield of 13.4% . Benzoyl chloride and β-alanine at the same time as the raw material , a yield of 85% of the completed build betamipron 22 . This thesis, the synthesis of all compounds were confirmed by spectroscopic corroboration correct .

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