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Method for synthesizing cefuroxime acid

A technology of cefuroxime acid and a synthesis method, applied in the field of chemistry, can solve problems such as difficult availability of raw materials, side reactions, dark product color, etc., and achieve the effects of saving one-step reaction, improving yield, and improving yield

Inactive Publication Date: 2011-02-16
SHANDONG JIANZHU UNIV +1
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  • Abstract
  • Description
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Problems solved by technology

It is mainly manifested in: (1) the hydrolysis reaction of the first step is carried out under strongly alkaline conditions, and under this condition, the lactam ring of 7-ACA can also be hydrolyzed to open the ring, resulting in a very low yield of hydrolysis; (2 ) the acid chloride reaction of the second step, reagents such as oxalyl chloride, phosgene, p-toluenesulfonyl chloride are commonly used as reagents, and these reagents have too high reactivity, easily generate more side reactions, and make the product color darker; and react Requirement is anhydrous reaction, operation requirement is higher, especially this process has very strong acid mist generation of irritation, serious to environmental pollution; (3) the carbamylation reaction of the 3-alcohol hydroxyl group in the third step, Utilize chlorosulfonyl isocyanate to react, the activity of reaction is on the low side, poor efficiency (reaction yield is only 75%), and this raw material is not easy to obtain

Method used

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  • Method for synthesizing cefuroxime acid
  • Method for synthesizing cefuroxime acid
  • Method for synthesizing cefuroxime acid

Examples

Experimental program
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Embodiment

[0050] (1) Preparation of SMIF-DP

[0051] In a 250ml four-necked flask, add (Z)-2-(2-furyl)-2-methoxyimino ammonium acetate (SMIA) 23.4g (0.125mol), dissolve in 75mlCH 2 Cl 2 Then add 6.5g (0.035mol) of tributylamine, stir and cool down to 0°C, put 25.5g (0.13mol) diethoxyphosphoryl thiochloride into the dropping funnel, dropwise add within 30min, continue the heat preservation reaction for 2 hour, HPLC detects that all SMIA reactions are complete, wash with water twice, each time with 25ml of water, stir and wash for 20min, separate liquids, and continue to use 50ml of 3% NaHCO at 0°C for the organic phase 3 aqueous solution and 50ml saturated brine, separated, the organic phase was dried with anhydrous magnesium sulfate, and filtered to obtain a light yellow organic solution compound (1) diethoxyphosphorylthio (Z)-2-furyl-2- Methoxyiminoacetate (SMIF-DP), without separation, the purity of the product detected by HPLC is 98%, and it is stored at low temperature for future ...

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Abstract

The invention provides a method for synthesizing cefuroxime acid. In the method, a phosphorus acyl active resin is subjected to hydrolysis reaction, the product of the hydrolysis reaction is subjected to aminoacylation, and a 3-decarba-moyl cefuroxime acid intermediate is synthesized by a one-pot method without separating the intermediate, the step of cefuroxime acid synthesis is saved, and the yield of the product is improved greatly.

Description

technical field [0001] The invention relates to a method for synthesizing cefuroxime acid, in particular to a method for synthesizing cefuroxime acid by using phosphoryl active esters, and belongs to the field of chemical technology. Background technique [0002] Cefuroxime (cefuroxime) is a second-generation cephalosporin first developed and listed by the British Glaxo Company in 1975. The pharmacopoeia of Britain, the United States, Japan and other countries and the pharmacopoeia of my country's 2000 edition are all recorded. Its good and balanced antibacterial activity cannot be replaced by other generations of antibiotics. [0003] The synthetic route of cefuroxime acid is to take 7-ACA as raw material at the earliest, introduce the protective group of amino group and carboxyl group successively in intermediate step, and finally take off protective group, obtain product through 8 steps reaction steps altogether, the yield of this method Particularly low at just 21%. A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/04C07D501/34
Inventor 任会学孙友敏贾祥风马永山
Owner SHANDONG JIANZHU UNIV
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