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Preparation method of 3-ethyl cefadroxil

A technology of ethyl cefadroxil and tert-butylation, which is applied in the field of preparation of 3-ethyl cefadroxil, can solve the problems of reducing drug efficacy, complex production process of cefadroxil, harm to human body, etc., and achieve operability Strong, high-purity, high-yield effects

Active Publication Date: 2018-08-14
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The production process of cefadroxil is relatively complicated, so some impurities or related compounds sometimes exist in the product
These impurities and related compounds will reduce the efficacy of the drug, and some will cause harm to the human body

Method used

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  • Preparation method of 3-ethyl cefadroxil
  • Preparation method of 3-ethyl cefadroxil
  • Preparation method of 3-ethyl cefadroxil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of compound Ⅱ

[0028] The reaction process is:

[0029]

[0030] Get 50 grams of 7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7-AVCA) suspended at 290 Add 54 ml of boron trifluoride diethyl ether slowly to the above solution in an ice bath, and react at 20°C for 6 hours to obtain a clear yellow solution. The reaction solution is slowly quenched with saturated sodium carbonate solution to neutral partial Alkaline (pH=9), suction filter the quenched reaction solution, extract the filtrate 3 times with 200 ml ethyl acetate, combine the organic phases, wash 3 times with 100 ml saturated brine, and wash the organic phase with anhydrous sodium sulfate Dry, filter and spin dry to obtain the crude product. The crude product was slurried with 300 ml of n-hexane to obtain compound II, 49.12 g, off-white solid, yield 78.7%.

[0031] Compound Ⅱ structural characterization results: 1 H-NMR (DMSO-d 6 )δppm: 6.72-6.79(dd,1H),5.53-5.57...

Embodiment 2

[0053] Synthesis of compound Ⅱ

[0054] The reaction process is:

[0055]

[0056] Take 10 grams of 7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7-AVCA) suspended in 150 In one milliliter of N,N-dimethylformamide, add 8.82 grams of sodium isooctanoate to the above reaction solution, then react at room temperature for 30 minutes to obtain a clear solution, add 12.1 grams of tert-butyl bromide to the reaction solution, and continue to react at room temperature for 12 hours , a yellow solution was obtained. Add 300 ml of water to the reaction solution, and extract 3 times with 150 ml of ethyl acetate, combine the organic phases, wash 3 times with 200 ml of saturated brine, dry the organic phase with anhydrous sodium sulfate, filter and spin dry to obtain a crude product. The crude product was purified once by column chromatography to obtain compound II, 3.8 g of off-white solid, with a yield of 30.4%.

[0057] Compound Ⅱ structural characteri...

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Abstract

The invention discloses a preparation method of 3-ethyl cefadroxil, and belongs to the field of drug synthesis. 7-amino-3-vinyl-8-oxo-5-thia-1-azabicyalo[4.2.0]oct-2-ene-2-carboxylate is taken as a raw material to synthesize the 3-ethyl cefadroxil by five-step reaction. According to the preparation method, the process design is reasonable, the operability is high, reaction conditions are simpler,the yield is high, and large-scale production can be realized. The 3-ethyl cefadroxil prepared by the method provides an important basis for performing scientific evaluation of quality, safety and efficiency, pharmacological research, pharmacokinetic research and the like on the 3-ethyl cefadroxil, also can serve as a possible new drug to be further researched and developed for treating urinary system, respiratory tract, skin, five sense organs, gastrointestinal tract infections and the like caused by staphylococcus, streptococcus, pneumococcus, escherichia coli and the like, and has importantapplication value.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of 3-ethylcefadroxil. Background technique [0002] Cephalosporins are the most potent class of widely used antibacterial drugs, which destroy the cell wall of bacteria and kill bacteria during the reproductive period. It has a strong selective effect on bacteria, but has almost no toxicity to humans. It has the advantages of broad antibacterial spectrum, strong antibacterial effect, penicillinase resistance, and allergic reactions are rare compared with penicillins. Therefore, it is an important antibiotic with high efficiency, low toxicity and wide clinical application. [0003] However, due to the long-term use of these antibiotics, bacteria are increasingly resistant to them. The development and production of antibiotic modification-semi-synthetic cephalosporins (SSC) has become an important way to solve this problem. Cefadroxil (cefadroxil) is the first ...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/04
CPCC07D501/04C07D501/22
Inventor 李砚涛刘锡张池崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
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