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Preparation method of Faropenem sodium

A technology of faropenem sodium and organic solvent is applied in the field of organic medicinal chemistry, can solve the problems of pressurization, high production cost, large amount of catalyst and the like, and achieves the effects of simple operation, low cost and high yield

Inactive Publication Date: 2009-11-25
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This document adopts palladium / carbon as catalyst to remove the allyl protecting group of carboxyl group, but this method will pressurize, and the consumption of catalyst is also larger simultaneously, and these will cause the problems such as industrialized production cost is on the high side

Method used

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  • Preparation method of Faropenem sodium
  • Preparation method of Faropenem sodium
  • Preparation method of Faropenem sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Sodium bicarbonate (5.2g, 61.4mmol) and deionized water (8mL) were placed in a reaction flask and stirred, and the olefin-based capture agent 5,5-dimethylcyclohexanedione (5.2g, 37.2mmol) was added in batches , continue to stir until the reaction solution is clear after the addition is complete; 3-Allyl carboxylate (20g, 61.4mmol) and ethyl acetate (80mL) solution, and after replacing the air in the reaction flask with nitrogen, quickly add palladium catalyst palladium dichloride (0.25g, 1.43mmol) and three Phenylphosphine (0.674g, 2.57mmol), stirred at 25°C for 5 hours, then cooled to 0°C and continued to stir for 0.5 hours, filtered, the filter cake was washed with ethyl acetate, washed with acetone-water (5:1, 240 mL) to obtain faropenem sodium (I) as a white crystalline powder. mp 163.1~164.2℃, [α] D25 =147.5°(c1.0, H 2 O).

[0036] Catalyst recovery: After the filtrate is decompressed to recover the solvent, it is washed with deionized water and dried to recove...

Embodiment 2

[0038] Sodium isooctanoate (10.2g, 61.4mmol) and deionized water (8mL) were stirred and dissolved in the reaction flask, and the olefin-based capture agent 5,5-dimethylcyclohexanedione (5.2g, 37.2 mmol), continue to stir until the reaction solution is clear after the addition; then add (1′R, 2″R, 5R, 6S)-6-[(1′-hydroxyethyl)-2″-tetrahydrofuryl] Penicillium Alkene-3-carboxylic acid allyl ester (20g, 61.4mmol) and acetone (80mL) solution, and after replacing the air in the reaction flask with nitrogen, add palladium catalyst palladium dichloride (0.25g, 1.43mmol) and triphenyl Phosphine (0.674g, 2.57mmol), stirred at 25°C for 5 hours, then cooled to 0°C and continued to stir for 0.5 hours, filtered, and the filter cake was washed with ethyl acetate, washed with acetone-water (5:1, 240mL ) recrystallization to obtain white crystalline powder faropenem sodium (I). mp 163.4~164.2℃, [α] D 25 =146.5°(c1.0, H 2 O).

[0039] Catalyst recovery: After the filtrate is decompressed to...

Embodiment 3

[0041] Sodium bicarbonate (5.2g, 61.4mmol) and deionized water (8mL) were placed in a reaction flask and stirred, and the olefin-based capture agent 5,5-dimethylcyclohexanedione (5.2g, 37.2mmol) was added in batches , continue to stir until the reaction solution is clear after the addition is complete; 3-Allyl carboxylate (20g, 61.4mmol) and ethyl acetate (80mL) solution, and after replacing the air in the reaction flask with nitrogen, quickly add the palladium catalyst bis(triphenylphosphine) palladium dichloride (1.0g , 1.43mmol), stirred at 25°C for 5 hours, then cooled to 0°C and continued to stir for 0.5 hours, filtered, washed the filter cake with ethyl acetate, and recrystallized with acetone-water (5:1, 240mL) to obtain White crystalline powder faropenem sodium (I). mp 163.3~164.2℃, [α] D 25 =147.5°(c1.0, H 2 O).

[0042] Catalyst recovery: After the filtrate is decompressed to recover the solvent, it is washed with deionized water and dried to recover the catalys...

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Abstract

The invention relates to a preparation method of Faropenem sodium (I). The preparation method of Faropenem sodium includes: using (1'R, 2''R, 5R, 65)-6-[(1'-R)-2''-tetrahydrofuran base]penem-3-carboxylic ether as raw material, R is hydroxyethyl, or tert-butyl dimethyl silica ethyl, in the presence of palladium catalyst and alkylene capturing agent, removing allyl group of carboxyl acid or cinnamon base protecting group, in the presence of alkaline producing Faropenem sodium; Or, B: when the R is tert-butyl dimethyl silica ethyl, in the presence of palladium catalyst, triphenylphosphine and alkylene capturing agent, after removing allyl group of carboxyl acid or cinnamon base protecting group, under the actions of fluorine hydride acid, ammonium acid fluoride or dilute acid, removing silicone base protecting group of hydroxyl group, under the action of alkali, producing Faropenem sodium, the alkylene capturing agent is 5, 5-dimethyl cyclohexanedione; the palladium catalyst contains palladiurn bichloride, mixture of palladiurn bichloride and triphenylphosphine, and di (triethoxy phosphine) palladiurn bichloride, etc.

Description

technical field [0001] The invention belongs to the field of organic medicinal chemistry, in particular to a preparation method of faropenem sodium (I). Background technique [0002] Faropenem sodium is a penem antibiotic developed by Suntory Corporation of Japan, which was first launched in Japan in 1997. Its structural formula is: [0003] [0004] It is the only antibiotic that can be taken orally and injectable among penems. It has antibacterial and bactericidal effects by preventing the synthesis of cell walls. It has high affinity for various penicillin-binding proteins (PBP), especially for the proliferation of cell bacteria. The high-molecular PBP has high affinity, is stable to various bacteria producing β-lactam molds, and has strong antibacterial activity against β-lactam mold-producing bacteria. It has a broad antibacterial spectrum, including aerobic Gram-positive bacteria (G + bacteria), aerobic Gram-negative bacteria (G - bacteria) and anaerobic bacteri...

Claims

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Application Information

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IPC IPC(8): C07D499/893C07D499/16B01J31/24B01J27/10A61P31/04
CPCY02P20/55
Inventor 陈芬儿黄建平赵磊古双喜
Owner FUDAN UNIV
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