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Studies on the Synthetic Process of Sulbenicillin Sodium

Author: XuXiaoZuo
Tutor: LiShaoHua
School: Jiangxi Medical College
Course: Medicinal Chemistry
Keywords: Anti-Pseudomonas aeruginosa drug Sulbenicillin Sodium Study on the Synthesis Therapeutics
CLC: R914
Type: Master's thesis
Year: 2005
Downloads: 304
Quote: 0
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Abstract


Objective: To study the synthesis of anti- Pseudomonas aeruginosa drug sulbenicillin . Sodium . Literature and experimental exploratory results , choose to optimize the synthetic route . And its structure was confirmed by various analytical methods . Method : In phenylacetic acid , 6 -APA as a starting material has been sulfonated into salt , ion exchange , acylation , amidation , a salt-forming six-step synthesis of the desired product . Phenylacetic acid , sulfur trioxide and dioxane complex sulfonated , under alkaline conditions have alpha - sulfosalicylic acid disodium salt by ion exchange alpha - sulfo phenylacetic acid . Which thionyl chloride acylated to obtain alpha - sulfo- phenylacetyl chloride , this step through the control of reaction temperature and time to obtain the desired product . alpha - sulfo- phenylacetyl chloride and 6-APA in the aqueous alkaline solution of a low temperature the Schotten - Banmann reaction occurs , and the solution in acidic and alkaline environments , respectively, with the corresponding solvent extraction , separation of the purification of the final product obtained sulbenicillin sodium Finally , the final product by IR , 1H NMR , mass spectrometry and other structure confirmation . Results: The synthesized by a six-step synthesis reaction to obtain the final product , the total yield was 25 % . And by IR , 1H NMR , mass spectrometry confirmed the structure of the product . Conclusions : 1 ) Preparation of alpha - sulfo- phenylacetic acid , using the resulting alpha - sulfo- phenylacetic acid , disodium salt in 70% ethanol and recrystallized twice and then by ion exchange was alpha - sulfo- phenylacetic acid of high purity . 2 ) reaction of the alpha - sulfo- phenylacetyl chloride and an aqueous alkaline solution of 6-APA low temperature , the reaction mixture system was slightly alkaline environment conducive to the progress of the reaction . 3) Preparation of sodium sulbenicillin , according to the literature using a water / acetone recrystallization effect is not ideal, directly by reaction in acidic and alkaline solutions , respectively, with the better the corresponding solvent extraction separation and purification results .

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