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A technology of cefuroxime acid and cefuroxime, applied in the field of preparation of intermediates, can solve the problems of low product purity, high drying temperature, long time and the like, and achieve the effects of high product purity, high product yield and short drying time
Active Publication Date: 2011-07-27
四平市精细化学品有限公司
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[0007] The second step of crystallization is carried out in the water phase, which cannot effectively remove the side reactants lactone and organic unsaponifiable matter, which affects the purity and stability of the product
At the same ti...
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Embodiment 1
[0035] (1), the preparation of 3-deformylamino cefuroxime (DCC):
[0036] Add 380ml of purified water and 200g of 7-ACA to the reaction flask, stir and dissolve with 200ml of 15% sodium hydroxide, then add 1500g of furoacetyl chloride dichloromethane solution with a prepared content of 12% into the above solution, and control the reaction temperature 0-15°C, stirred for 2 hours, and kept the pH of the solution at 5.5-7.5 during the reaction. Stand still for 10-30 minutes after the reaction, separate the water phase, extract the organic phase once with 50ml of purified water, combine the water phase, add 80ml of methanol, cool to -25~-30°C, add 15% (mass) sodium hydroxide 200g, stirred and reacted for 30 minutes, added 80ml of glacial acetic acid, then adjusted the pH of the feed solution to 1.0-2.0 with 25% hydrochloric acid, filtered after stirring for 15 minutes, washed the filter cake DCC with 180ml of purified water, and vacuum-dried at 40°C until the water content Less t...
Embodiment 2
[0040] Preparation of cefuroxime acid:
[0041] The preparation of 3-deformamidocefuroxime (DCC) is the same as in Example 1, and DCC 100g is prepared according to (1) in Example 1, and 300ml of tetrahydrofuran is added for dissolution, and cefuroxime acid is prepared according to the method in (2) in Example 1 To the reaction solution, add 220ml of ethyl acetate and 360ml of dichloromethane, then add sodium bicarbonate solution, adjust the pH to 7.5, stir for 10 minutes, let it stand for layers, extract lactone and unsaponifiable matter from the organic phase, and add Add 660ml of ternary composite solvent, then add 31% hydrochloric acid to adjust PH=2.0, let stand for 25 minutes, then separate the liquid, carry out vacuum distillation on the organic phase, stop distillation when the solution distillate is 300ml, cool to 5~10°C, Stir for 2 hours. After vacuum filtration, the filter cake was vacuum-dried at 40° C. for 2 hours to obtain 102.18 g, with a purity of 99.31%, a wat...
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Abstract
The invention discloses a preparation method of high-purity cefuroxime acid which is an intermediate for synthesizing second-generation cephalosporins cefuroxime sodium and cefuroxime axetil. The preparation method comprises the following steps: based on 7-aminocephalosporanic acid (7-ACA) as a raw material, carrying out an N-acylation reaction on the 7-ACA and furoyl acetylcholine at the 7-position; at a low temperature, hydrolyzing 3-acetyl with a sodium hydroxide solution, crystallizing, filtering and drying so as to obtain the intermediate 3-deformamido cefuroxime acid (DCC); quantitatively adding the DCC in a tetrahydrofuran solvent, dropwise adding chlorosulfonyl isocyanate for a nucleophilic addition reaction so as to generate chlorosulfonyl cefuroxime acid, and adding purified water for hydrolysis so as to prepare a cefuroxime acid reaction liquid; adding sodium bicarbonate for salifying; removing by-reactant lactone and other unsaponifiable impurities in the reaction liquid with a ternary compound extracting agent of dichloromethane, ethyl acetate and tetrahydrofuran, layering, and adding hydrochloric acid in a water phase for acidification; adding the ternary compound extracting agent to extract and separate out the cefuroxime acid; and removing water-soluble impurities, crystallizing and filtering a distilled organic phase, and then drying so as to obtain the high-purity cefuroxime acid with the purity of more than or equal to 99%.
Description
technical field [0001] The invention relates to a method for preparing intermediates for synthesizing the second-generation cephalosporin antibiotics cefuroxime axetil and cefuroxime sodium, in particular to a method for preparing high-purity cefuroxime acid. Background technique [0002] Cefuroxime acid is an intermediate in the synthesis of the second-generation cephalosporin antibiotics cefuroxime axetil and cefuroxime sodium. Cefuroxime antibiotics have a broad-spectrum antibacterial effect and a wide range of applications. They can be used for respiratory tract infections, ENT infections, urinary system infections, skin and soft tissue infections, bone and joint infections, gonorrhea, including sepsis and meninges caused by sensitive bacteria. and other infections, it is the leading variety of second-generation cephalosporin antibiotics. Cefuroxime acid is an irreplaceable intermediate of cefuroxime antibiotics. There are two methods for preparing cefuroxime acid, one...
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