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A methoxycefoxitin and methoxyl technology, applied in the field of impurity analysis in drug synthesis, can solve problems such as affecting drug efficacy, toxic and side effects, and achieve the effects of clinical safety use guarantee, simple steps and low cost
Active Publication Date: 2019-09-06
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] The chemical reaction formula for the preparation of (RS)-α-trichloromethyl-2-thiophenemethanol
[0037]
[0038] Add 84g (1.0mol) of thiophene, 500ml of n-heptane and 147g (1.0mol) of chloral into a 1000ml three-necked flask, stir, heat up to reflux, cool down to room temperature after the reaction, concentrate under reduced pressure to recover the solvent, and depressurize the residue Distillation, collecting 98 ~ 100 ℃, 1.0mmHg fraction, yield about 46g.
Embodiment 2
[0040] Preparation of (RS)-α-trichloromethyl-2-thiophenemethanol
[0041] Add 84g (1.0mol) of thiophene, 500ml of n-heptane and 147g (1.2mol) of chloral into a 1000ml three-necked flask, stir, heat up to reflux, cool down to room temperature after the reaction, concentrate under reduced pressure to recover the solvent, and decompress the residue Distillation, collecting 98 ~ 100 ℃, 1.0mmHg fraction, yield about 52g.
Embodiment 3
[0043] The chemical reaction formula for the preparation of (RS)-α-methoxy-2-thiophene phenylacetic acid
[0044]
[0045]Under nitrogen protection, add 100ml methanol and 11.2g (0.2mol) potassium hydroxide into a 500ml three-necked flask, stir to dissolve, cool to -5~0°C, add 11.6g (0.05mol) (R,S)-α-tri A solution of chloromethyl-2-thiophene methanol in 30ml of methanol, stirred, slowly heated to reflux, cooled to room temperature after the reaction, concentrated under reduced pressure to remove the solvent, added 50ml of methyl tert-butyl ether to the residue, and used under stirring Adjust the pH to 3.0 with 0.1N dilute hydrochloric acid, separate the organic layer, extract the aqueous layer with methyl tert-butyl ether again, combine the organic layers, wash with brine, dry over anhydrous sodium sulfate, filter, and concentrate 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, belonging to the field of impurity analysis in drug synthesis. Background technique [0002] 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 cephamycin antibiotic developed by Merck Company of the United States. [0003] In the process of new drug research and development, the quality of the drug is an important criterion to measure the quality of the drug. The quality of the drug firstly 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 ingredient of a drug is an important symbol reflecting 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. Impurities in drugs are chemical substance...
Claims
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