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A kind of synthetic method of ertapenem sodium

A technology of ertapenem sodium and a synthesis method, which is applied in the field of drug synthesis and can solve the problems of complicated post-processing, poor purity, and high residues of heavy metals in products

Active Publication Date: 2022-04-29
SHENZHEN HAIBIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of this, the present application provides a synthesis method of ertapenem sodium, which effectively solves the existing ertapenem synthesis methods that require cumbersome post-processing, low production capacity, high heavy metal residues in the product, and poor purity. technical problem

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  • A kind of synthetic method of ertapenem sodium
  • A kind of synthetic method of ertapenem sodium
  • A kind of synthetic method of ertapenem sodium

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Embodiment 1

[0042] The embodiment of the present application provides the preparation method of the compound shown in formula 1, specifically including:

[0043] According to the following synthetic route, dissolve 94.2g of carbapenem core MAP and 57.3g of ertapenem side chain hydrochloride in 600g of DMF, add 60.8g of tetramethylguanidine dropwise at -50°C, and stir Condensation reaction, after the reaction is completed, the pH value of phosphoric acid is adjusted to 5, and the acid-adjusted feed solution is added to water for crystallization to obtain a compound represented by formula 1 as a solid. Its purity is 98.9%.

[0044] .

Embodiment 2

[0046] The embodiment of the present application provides the preparation method of ertapenem sodium, which specifically includes:

[0047] Add 93g of water, 50g of methanol, 24g of n-propanol, 53g of ethyl acetate, 10g of the compound shown in formula 1, 4.2g of sodium bicarbonate into the three-necked flask, stir and dissolve, add to the hydrogenation kettle, and simultaneously add 1.13g of palladium carbon, Replace with nitrogen, add hydrogen to 2.0Mpa, react at 20°C for 3 hours, after the reaction is completed, filter, separate liquids to obtain a product solution, use aqueous hydrochloric acid to adjust the pH value of the product solution to 6.0, add an equal volume of methanol and n-propanol to carry out After crystallization and drying, 6.7 g of white ertapenem sodium solid was obtained, with a molar yield of 82.1%, an HPLC purity of 99.09%, and a heavy metal content of <10 ppm.

[0048] Measure the chromatogram of the ertapenem sodium that the embodiment of the presen...

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Abstract

The application belongs to the technical field of pharmaceutical synthesis, and in particular relates to a synthesis method of ertapenem sodium. The application provides a synthetic method of ertapenem sodium, comprising the following steps: under the conditions of alkali, catalyst and hydrogen atmosphere, mixing the compound shown in formula 1 with a mixed solvent for hydrogenation reaction, filtering to obtain the product solution, acetic acid Extract and purify with ethyl ester, adjust the pH value of the water phase to 4~7 to obtain an acidic product solution; add a crystallization solvent to the acidic product solution for crystallization to obtain ertapenem sodium; the ertapenem sodium has Structure shown in formula 2. The present application provides a method for synthesizing ertapenem sodium, which effectively solves the technical problems existing in the existing ertapenem synthesis methods that require cumbersome post-processing, low production capacity, high residues of heavy metals in the product, and poor purity.

Description

technical field [0001] The application belongs to the technical field of pharmaceutical synthesis, and in particular relates to a synthesis method of ertapenem sodium. Background technique [0002] Ertapenem (Ertapenem, structural formula is ) is a carbapenem antibiotic with broad-spectrum antibacterial properties, jointly developed by Merck and AstraZeneca, its chemical name is (4R, 5R, 6S)-6-[(3S,5S)- 5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-nitrogen Heterobicyclo[3.2.0]hept-2-ene-2-carboxylic acid. [0003] At present, the mainstream method for industrial production of penem compounds is: hydrogenation of palladium carbon followed by deprotection, and ertapenem is also used for hydrogenation and deprotection. However, deprotection using this method faces a problem of excessive heavy metals. At the same time, due to the instability of ertapenem itself, the cumbersome post-processing operation makes the product seriousl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D477/08C07D477/20
CPCC07D477/08C07D477/20
Inventor 姜能江林楠棋欧军王东幸志伟孙万鹏
Owner SHENZHEN HAIBIN PHARMA
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