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Study on the Synthetic Process of Ceftizoxime

Author: LiHang
Tutor: YuZuoFeng；FuDeCai
School: Hebei University of Science and Technology
Course: Chemical processes
Keywords: Cephalosporin Ceftizoxime sodium 7-ANCA AE activated ester synthetic process
CLC: TQ465.1
Type: Master's thesis
Year: 2011
Downloads: 101
Quote: 0
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Abstract


Ceftizoxime sodium, one of the third generation cephalosprins for injection use,was described in detail, including its antibiotic mechanism, pharmacological properties, clinical effects and related synthetic methods. The synthetic process of Ceftizoxime was studied. After investigation of a series of synthetic routes of Ceftizoxime, we determined the best route which was suitable for scale production.The synthesis of 7-amino-3-nor-3-cephem-4-carboxylic acid (7-ANCA) was studied, which was an important intermediate of Ceftzoxime.3-Hydroxy-7-beta-phenylacetylamino cephem-4-caroxylic acid diphenylmethyl ester (HCA) was synthesized from 3-oxo-7-phen yl-acetylaminocphem-4-carboxylic acid diphenylmethyl ester 3-hydroxycephem toluene complex) by reduction with sodium borohydride. The yield of product was about 85%. 3-Hydroxy-7-beta-phenylacetyl-aminocephem-4-carboxylic diphenylethyl este(BCD) was synthesized from HCA and methanesulfonyl chloride, in dichloroethane solvents.The yield of product was bout98.5%.3-hydroxy-7-beta-phenylacetylamino cephem-4-carboxylic was synthesized from BCD,aluminum trichloride and anisole, which deprotected the carboxyl protecting group. The yield of product was about 98%. The products of 3-hydroxy-7-beta-phenylacetylaminocephem-4-carboxylic was enzyatic hydrolyed to deprotect the amino protecting group, and 7-ANCA was obtained. The yield of product was about75%. The total yield of 7-ANCA was about61%, the purity of product was 99.9%.It was appreciated that the preparation of ceftizoxime by reaction of7-amino-3-nor-3-cephem-4-carboxylic acid (7-ANCA) with 2-(2-aminothiazol-4-thiazolyl)-2-[[(Z)metho-xy]imino]acetic acid S-mercapto benzothiazolylester (activated ester), in the condition of triethylamine. The yield of product was about 91.8%. The products of ceftizoxime sodium was synthesized by ceftizoxime sodium 2-ethylhexanoate.The optimum conditions were as follows:in isopropanol solvent, volume ratio of isopropyl to water was 10:1, the yield of ceftizoxime sodium was 91.8%.The total yield of ceftizoxime sodium was about86.8%, the purity of product was 99.34%(HPLC).The chemical structures of ceftizoxime sodium had been characterized by means of IR and1-NMR. The product quality accords with the standard of Chinese pharmacopoeia.

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Antibiotics manufacture > Penicillin and its derivatives
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