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

Improvement in the Synthesis of (Z)-2-Methoxyimino-2-Furylacetic Acid Ammonium Salt

Author LiLiLi
Tutor WangQiuFen
School Jinan University
Course Chemical Engineering
Keywords Cefuroxime SMIA 2-acetyl furan synthesis
Type Master's thesis
Year 2012
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Cephalosporin antibiotics are widely used in clinical treatment of diseases caused bypathogenic by pathogenic bacteria in recent years. So far, they have been developed into theforth generation. Cefuroxime(cefuroxime sodium and cefuroxime axetil), the second gener-ation cephalosporins drugs, with broad-spectrum antimicrobial activity and low toxicitycharacteristics of cephalosporin antibiotics has a good momentum of development in recentyears. It has been found in the world medicine sales charts for several years, and it has a hugeconsumer market and good prospects for development.(z)-2-Methoxylimino-2-furylactic acid ammonium salt, which is short for SMIA, is animportant intermediate for the production of cefuroxime. This article is a study on thesynthesis route and synthesis process, aimed at improving the production process whichstarted from2-acetyl furan for the synthesis of SMIA to enhance the product’s yield. Thetemperature、pH、reaction time、and reaction conditions were determined for its industrial-ization. The improved synthetic method of SMIA were researched, and the procedure is morehelpful for the industrial production.The experiment results showed as the following: the oxidation of2-acetyl furan hasmade a good oxidation effect in the condition of using copper sulphate as a catalyst catalytic,2-acetyl furan oxidation conversion rate increased to93%,2-oxo-2-furan acetic acid does notneed to be removed from the reaction solution, reacted with methoxamine hydrochloridedirectly,2-methoxyimino-2-cis-selectivity of furan acetic acid’s yield reached85%(HPLC),and (Z)-2-methoxyimino-2-furylacetic acid ammonium salt crude purity up to99.8%. Theinfluencing factors on the reaction, including metal ions、temperature、pH and time on theyield and quality have been determined. It is suggested that the total yield up to68%and99.8%measured purity of the product can be obtained under the following conditions:n(copper sulphate):n(2-acetylfuran) equals1:97,2-acetylfuran oxidation temperature65℃,m(98%sulphate acid):m(2-acetylfuran)=0.186:1, m(35%phosphoric acid):m(2-acetylfuran)=0.65:1, oximation temperature20℃and pH4.5, crystallization temperature0℃and pH8.Product quality meet to domestic and international requirements. With copper sulphateprocess, the novel process increased yield to above15%, reduced production costs. The ptimized synthesis route has the advantages of the following: the reaction conditions is mild, the products’ quality is stable, and has a good reproducibility. The results forthe synthesis of (z)-2-Methoxylimino-2-furylactic acid ammonium salt has an important guid-ing significance for industrial production, the product yield has a substantial increase. Andprovide a new way on the metal ion catalyzed oxidation study.

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