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Preparation method of cefditoren pivoxil ring-opening dimer

A technology of cefditoren pivoxil and cefditoren pivoxil, which is applied in the field of preparation of cefditoren pivoxil ring-opening dimer, can solve the problems of limited popularization and application, harsh reaction conditions, long reaction route, etc., and achieve raw material economy Easy to obtain, simple reaction and operation, and the effect of reducing synthesis cost

Active Publication Date: 2021-09-24
湖北凌晟药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Said route has obtained the high-purity cefditoren pivoxil ring-opening dimer, but the whole reaction route is long, and in the polymerization step, irritating methanesulfonyl chloride has been adopted, and the whole reaction environment must be controlled in anhydrous, Below -20°C, the reaction conditions are harsh, high risk and unfavorable for production
Not only that, in the step of deprotection group, the palladium carbon catalyst that takes is expensive, does not have economy, and its popularization and application is restricted

Method used

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  • Preparation method of cefditoren pivoxil ring-opening dimer

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Embodiment 1

[0027] This embodiment provides a kind of preparation method of cefditoren pivoxil ring-opening dimer, the specific steps are as follows:

[0028] At room temperature, a mixed solvent with a dichloromethane / ethanol volume ratio of 5:1 was prepared. Get cefditoren pivoxil 20g (32.2mmol), join in 200mL mixed solvent, stir until dissolving. The temperature was raised to 55° C. for the reaction, and the peak of the ring-opened dimer of cefditoren pivoxil was monitored by HPLC, and the reaction was terminated. After cooling down to room temperature, the solvent was evaporated to dryness using a rotary concentrator to obtain a light yellow crude product. Purified by silica gel column chromatography, eluted with dichloromethane-methanol 80:1 to obtain a light yellow solid, transferred to an oven at 40°C and dried under reduced pressure for 3 to 5 hours to obtain 8.5 g of dry product, the purity of which was detected by HPLC was 97.3% (see figure 1 ).

Embodiment 2

[0030] This embodiment provides a kind of preparation method of cefditoren pivoxil ring-opening dimer, the specific steps are as follows:

[0031] At room temperature, a mixed solvent with a dichloromethane / methanol volume ratio of 8:1 was prepared. Get cefditoren pivoxil 20g (32.2mmol), join in 220mL mixed solvent, stir until dissolving. The temperature was raised to 50° C. for the reaction, and the peak of the ring-opened dimer of cefditoren pivoxil was monitored by HPLC, and the reaction was terminated. After cooling down to room temperature, the solvent was evaporated to dryness using a rotary concentrator to obtain a light yellow crude product. Purified by silica gel column chromatography, eluted with chloroform-methanol 70:1 to obtain a light yellow solid, transferred to an oven at 40°C and dried under reduced pressure for 3-5 hours to obtain 8.1 g of dry product, the purity of which was detected by HPLC was 95.4%.

Embodiment 3

[0033] This embodiment provides a kind of preparation method of cefditoren pivoxil ring-opening dimer, the specific steps are as follows:

[0034] At room temperature, a mixed solvent with a volume ratio of chloroform / ethyl acetate of 10:1 was prepared. Get cefditoren pivoxil 20g (32.2mmol), join in 250mL mixed solvent, stir until dissolving. The temperature was raised to 65° C. for the reaction, and the peak of the ring-opened dimer of cefditoren pivoxil was monitored by HPLC, and the reaction was terminated. After cooling down to room temperature, the solvent was evaporated to dryness using a rotary concentrator to obtain a light yellow crude product. Purified by silica gel column chromatography, eluted with dichloromethane-ethanol 100:1 to obtain a light yellow solid, transferred to an oven at 40°C and dried under reduced pressure for 3-5 hours to obtain 8.3 g of a dry product, the purity of which was detected by HPLC was 96.9%.

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Abstract

The invention provides a preparation method of a cefditoren pivoxil ring-opening dimer, which comprises the steps of dissolving cefditoren pivoxil in a solvent, reacting at the temperature of 50-70 DEG C to obtain a crude product, and purifying the crude product to obtain the cefditoren pivoxil ring-opening dimer. Compared with the prior art, the method has the beneficial effects that the cefditoren pivoxil is directly subjected to ring opening and polymerization reaction in the solvent through heating, the reaction operation is simple, the raw materials are economical and easy to obtain, the purity of the cefditoren pivoxil is more than 95%, and the synthesis cost is effectively reduced.

Description

technical field [0001] The invention relates to the field of drug impurity synthesis, in particular to a preparation method of cefditoren pivoxil ring-opened dimer. Background technique [0002] Cefditoren Pivoxil (Cefditoren Pivoxil), the chemical name is (6R,7R)-2,2-dimethylpropionyloxymethyl-7-[(Z)-2-(2-amino-4-thiazolyl) )-2-methoxyiminoacetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5- Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, the chemical structure of which is shown below: [0003] [0004] Cefditoren pivoxil has a wide range of antibacterial effects, and it is mainly used clinically to treat skin infections, mastitis, perianal abscess, genitourinary system infections, cholecystitis, cholangitis, otitis media, sinusitis, periodontitis, hordeolum , Dacryocystitis, pharyngitis, tonsillitis, acute and chronic bronchitis, etc. After absorption, the drug is metabolized into cefditoren in the intestinal wall. The mechanism of action is to inhibit t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/04C07D501/24
CPCC07D501/04C07D501/24
Inventor 何健黄金果金联明门万辉王腾
Owner 湖北凌晟药业股份有限公司
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