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Synithesis of the Methoxy Cephalosporins Intermediate and Exploration of Cefotetan Precursors

Author: WangYing
Tutor: JinNingRen；ZhaoDeMing
School: Zhejiang University of Technology
Course: Chemical processes
Keywords: Methoxy cephalosporin intermediates Cefotetan precursor Synthesis and Exploration 7β-amino -7α- methoxy-3 - ( 1 - methyl - 1H - tetrazol -5 - ylthiomethyl) -3 - cephem-4 - carboxylate Diphenylmethyl 7-MAC 7 - 7-DTMC toluene sulfur imino -3 - (1 - methyl -1H-tetrazole -zol-5 - ylthiomethyl ) -3 - cephem-4 - carboxylic acid diphenylmethyl ester Diphenyldiazomethane DPM
CLC: TQ465
Type: Master's thesis
Year: 2008
Downloads: 92
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Abstract


This paper describes the overview of the development of β- lactam antibiotics in the cephalosporin , cephalosporin introduced Alternate synthetic route tanks and precursors , the focus key intermediates for the the raw chemical synthesis methoxy ceph 7β-amino- 7-ACA -7α- methoxy-3 - (1 - methyl - 1H - tetrazol -5 - ylthiomethyl ) -3 - cephem -4 - carboxylic acid diphenylmethyl ester (7-MAC) , and the synthesis process other intermediates , as well as key raw materials diphenyldiazomethane (DPM) and methylthiophenol chloride (TSC) of the synthetic routes and methods . DPM various oxidants synthesis system in synthesized technically , research , and development of hydrogen peroxide as the oxidant efficiency, a clean preparation DPM innovation process; 7-ACA with 5-MMT as raw material by solvent nucleophilic substitution of synthetic base intermediate 7-AMCA and carboxyl protecting synthesis intermediates with DPM 7-DAMC other processes ; synthesis after 7-DAMC raw materials of three different amino protection route 7-MAC exploration test and screening comparison established the synthetic amino protected intermediates 7-DTMC mathematical model ; while exploring the 7-MAC process route for the synthesis of cephalosporin cefotetan precursor . The results show that : 1) the successful development of the synthesis of hydrogen peroxide as the oxidant DPM cleaner production processes , optimized by orthogonal experiment 94.25% yield of 90.83% purity the DPM ; 2 ) 7- ACA mesylate in acetic acid solvent catalyst to give a yield of 73.93% , a purity of 97.15% of the 7 - the AMCA using DPM carboxy protecting purity of 97.93% , 48.72% yield of 7 - DAMC ; 3 ) Synthesis of 7-MAC the TSC or aromatic aldehyde pairs 7-DAMC amino protected route is preferred , with TSC amino protecting synthesis of intermediates 7 - DTMC after regression orthogonal combination design optimization test , respectively, prepared by a purity of 97% , yield 78% of the 7-DTMC and a yield of 63.51% of the 7- MAC ; 4 ) cephalosporin cefotetan precursor synthesis route should be selected 7-MAC condensation hydrolysis of the raw materials with bromoacetyl bromide process route is better . Successful research as raw material through Step 6 to 7-ACA and 5-MMT reaction chemical synthesis of key intermediate 7 - MAC process , the total yield of 17.7% , to optimize the synthesis of key raw materials and intermediates in the preparation process conditions, especially the serious pollution of the steps has been improved , and laid a solid foundation for industrialization generated .

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Antibiotics manufacture
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