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A technology of methoxycefoxitin and methoxy, which is applied in the field of impurity analysis in drug synthesis, can solve problems such as toxic and side effects and affect drug efficacy, and achieve the effects of simple steps, guaranteed clinical safety and low cost
Active Publication Date: 2020-09-18
CHONGQING MEDICAL & PHARMA COLLEGE
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Problems solved by technology
The content of the active ingredient of a drug is an important indicator of the purity of the drug, and the impurities in the drug directly affect the efficacy of the drug and may cause toxic and side effects
Method used
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Embodiment 1
[0036] Chemical reaction formula for the preparation of (RS)-α-trichloromethyl-2-thiophene methanol
[0037]
[0038] In a 1000ml there-necked flask, add 84g (1.0mol) thiophene, 500ml n-heptane and 147g (1.0mol) trichloroacetaldehyde and stir, heat up to reflux, cool down to room temperature after the reaction, concentrate under reduced pressure to recover the solvent, and the residue is decompressed Distillation, collect 98~100 ℃, 1.0mmHg fraction, yield about 46g.
Embodiment 2
[0040] Preparation of (RS)-α-trichloromethyl-2-thiophene methanol
[0041] In a 1000ml there-necked flask, add 84g (1.0mol) thiophene, 500ml n-heptane and 147g (1.2mol) trichloroacetaldehyde and stir, heat up to reflux, cool down to room temperature after the reaction, concentrate under reduced pressure to recover the solvent, and the residue is decompressed Distillation, collect 98~100 ℃, 1.0mmHg fraction, yield about 52g.
Embodiment 3
[0043] The chemical reaction formula for the preparation of (RS)-α-methoxy-2-thiophenephenylacetic acid
[0044]
[0045]Under nitrogen protection, add 100ml methanol and 11.2g (0.2mol) potassium hydroxide to a 500ml three-necked flask, stir to dissolve, cool to -5~0°C, add 11.6g (0.05mol) (R,S)-α-trimonium A solution of chloromethyl-2-thiophene methanol in 30 ml of methanol was stirred, slowly heated to reflux, cooled to room temperature after the reaction, concentrated under reduced pressure to remove the solvent, added 50 ml of methyl tert-butyl ether to the residue, stirred with 0.1N dilute hydrochloric acid was adjusted to pH 3.0, the organic layer was separated, the aqueous layer was extracted with methyl tert-butyl ether again, the organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain about 6.2 g of product .
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Abstract
The invention discloses a preparation method of (RS)-methoxy cefoxitin, which is characterized by comprising the following steps: (1) taking thiophene as an initial raw material, n-heptane as a reaction solvent, reacting with trichloroacetaldehyde, and distilling under reduced pressure after the reaction; (2) reacting the product of the step (1) with methanol in the presence of alkaline substancesto prepare (RS)-alpha-methoxy-2-thiophenephenylacetic acid; (3) dissolving the (RS)-alpha-methoxy-2-thiophenephenylacetic acid in an organic solvent, adding a first organic base, stirring and clarifying, and dripping methanesulfonyl chloride or pivaloyl chloride for later use; adding HACA and an organic solvent into another reaction vessel, adding a second organic base, and stirring the mixture until the mixture is clarified for later use; slowly dripping a solution B into a solution A at below -30 DEG C; then dropwise adding chlorosulfonyl isocyanate to react to obtain white-like crystallinepowder; and (4) reacting the white-like crystalline powder with sodium methoxide to obtain a product. The purity of the product is high.
Description
technical field [0001] The invention relates to a preparation method of (RS)-methoxycefoxitin, and belongs to the field of impurity analysis in drug synthesis. Background technique [0002] Cefoxitin (Cefoxitin), the chemical name is (6R, 7S)-3-carbamoyloxymethyl-7-methoxy-8-oxo-7-[2-(2-thienyl)acetamido] -5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a semi-synthetic cephalosporin antibiotic developed by Merck Company in the United States. [0003] In the process of new drug research and development, the quality of the drug is an important criterion for measuring the quality of the drug. The quality of the drug first depends on the efficacy and side effects of the drug itself, that is, the effectiveness and safety of the drug. The content of the active ingredients of a drug is an important indicator of the purity of the drug, and impurities present in the drug directly affect the efficacy of the drug and may lead to toxic and side effects. Drug impurities are o...
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