Preparation method for Aspoxicillin

A technology of apicillin and aspartic acid, which is applied in the field of the preparation of the first product of apicillin, can solve the problems of increasing the preparation cycle, unsafe industrial production, inconvenient deprotection and the like, and achieves easy operation, toxicity and environmental impact. The effect of low pressure, easy storage and transportation

Inactive Publication Date: 2012-04-11
SOUTHWEST JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the synthesis process, thionyl chloride is used to react to generate 2-aminomethylamine carbonyloxypropionic acid. This step generates a large amount of black solid with many by-products, and it is reacted with hydrogenation deprotection group, which is very unsafe for industrial production.
[0013] Tang Guang'an from China Pharmaceutical University reported in the literature that apoxicillin was synthesized by the acid anhydride method. This method first uses 2-nit

Method used

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  • Preparation method for Aspoxicillin
  • Preparation method for Aspoxicillin
  • Preparation method for Aspoxicillin

Examples

Experimental program
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Embodiment 1

[0039] The preparation of embodiment 1 apoxicillin

[0040] 1) synthesis of aspartate hydrochloride

[0041] Reaction formula:

[0042]

[0043] operate:

[0044] Add 100g (0.75mol) of D-Asp to 54ml (0.75mol) of thionyl chloride and 500ml of methanol liquid under stirring at a temperature of 0-10°C (thionyl chloride is added dropwise to methanol under stirring, and the exothermic phenomenon is obvious during this process ), the reaction solution was colorless and transparent, and after the addition, continued to stir at room temperature and reacted for 40 minutes before doing TLC analysis (TLC: n-butanol: water: acetic acid = 3: 1: 1, the product was yellow-brown on the top, and the raw material was yellow-brown on the bottom). purple), concentrated under reduced pressure at 40°C to dryness to obtain a white solid, and then recrystallized the obtained solid with 50ml of methanol and 200ml of ethyl acetate, and a large amount of white solid was precipitated, filtered with ...

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Abstract

The invention discloses a preparation method for Aspoxicillin. D-aspartic acid is added into a mixture liquid of sulfuryl chloride and carbinol under a low temperature of zero to prepare D-aspartic acid methyl ester hydrochloride; the obtained D-aspartic acid methyl ester hydrochloride and triethylamine are reacted in ethanol to obtain D-aspartic acid methyl ester educt; the D-aspartic acid methyl ester educt and methylamine aqueous liquid with a concentration of 40 percent are reacted in a room temperature to prepare aspartic formamide; the aspartic formamide, ethyl acetoacetate and potassium hydroxide are reacted in isopropanol to prepare diene salt (D-2-amino-3N-methylamino oxo-propionic acid diene formamide); the diene salt and pivaloyl chloride are reacted in acetone under the catalysis of pyridine to obtain active anhydride; then the active anhydride is condensed and further protected by deacidification to obtain a target product-crude product of Aspoxicillin. The preparation method for Aspoxicillin has the advantages of cheap and easily-obtained reagent, lower toxicity and lower environment pressure, stable and simple technological operation and high yield.

Description

technical field [0001] The invention relates to the technical field of chemical pharmacy, especially the preparation of primary apoxicillin. Background technique [0002] Apoxicillin is a synthetic penicillin that inhibits the synthesis of bacterial cell walls. Using different parts of Escherichia coli K-12 membrane, the results of affinity for penicillin-binding protein show that this product has high affinity for PBPS-2, 1A, 1BS, and 3 sites, and has strong inhibition on the formation of peptidoglycan bridging effect. This product has strong antibacterial effect on Staphylococcus, Streptococcus, Enterococcus, and Pneumococcus of Gram-positive bacteria, excellent antibacterial effect on Escherichia coli and influenza bacilli of Gram-negative bacteria, and has excellent antibacterial effect on anaerobic bacteria Bacteroides have antimicrobial properties. Combined use with aminoglycoside system antibiotics can achieve synergistic effect. Especially when combined with gent...

Claims

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Application Information

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IPC IPC(8): C07D499/68C07D499/04
Inventor 陆群徐洪贵
Owner SOUTHWEST JIAOTONG UNIV
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