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Preparation method for tebipenem pivoxil

A technology of tipipenem and pivate, which is applied in the field of preparation of tipipenem and pivate, can solve the problems of difficult preparation and storage, increase of production cost, equipment corrosion, etc., and achieve simple operation and simple post-processing , the effect of high purity

Inactive Publication Date: 2012-11-14
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology makes it easier than previous methods because there are no steps needed beforehand or they can be stored safely without losing their ability to work properly with water. It also has fewer components making them more cost-effectively compared to existing technologies like lithium nitroprusside. Additionally, this new process allows for higher yields while maintaining good quality products due to its simplified manufacturing processes.

Problems solved by technology

This patented technical solution describes how tispenems like Penimopristone were discovered during World War Against Antibiosis Research Programme 1987. However, these new molecules had weakened their effectiveness due to poor solubility caused by certain substituents present at specific positions within them. To overcome such issues, another approach has been proposed involving modifying existing structures containing other chemical groups involved.

Method used

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  • Preparation method for tebipenem pivoxil
  • Preparation method for tebipenem pivoxil
  • Preparation method for tebipenem pivoxil

Examples

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Embodiment 1

[0042] Under nitrogen protection, compound (IV) (20.8g, 0.06mol), tributylphosphine (24.6g) and water (2.16g) were added to 300mL acetonitrile, stirred at room temperature for 40min, and the reaction solution was cooled to -10°C , then added compound (III) (57.4 g, 0.10 mol) and diisopropylethylamine (20.9 mL, 0.12 mmol) dropwise, and reacted at -10°C for 4 h after the dropwise addition.

[0043] Add 500mL ethyl acetate and 200mL water, adjust the aqueous solution to an acidic pH of 4.6, separate the layers, take the water layer, adjust the alkaline pH of the water layer to 7.8, extract twice with ethyl acetate (600mL*2), wash the organic layer with water, and saturated salt Washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated.

[0044] Add 100mL of ethyl acetate, heat to dissolve, add dropwise 100mL of n-hexane, slowly cool to below 0°C, stir at the same temperature for 2h, filter and dry to obtain 47.1g of the target compound (I), with a yield...

Embodiment 2

[0046] Under argon protection, compound (IV) (20.8g, 0.06mol), tributylphosphine (26.7g) and water (2.16g) were added to 500mL acetonitrile, stirred at room temperature for 50min, and the reaction solution was cooled to -10 °C, compound (III) (57.4 g, 0.10 mol) was added, triethylamine (10.1 g, 0.10 mmol) was added dropwise, and reaction was carried out at -10 °C for 7 h after the dropwise addition.

[0047] Add 400mL ethyl acetate and 200mL water, adjust the aqueous solution to an acidic pH of 4.6, separate the layers, take the water layer, adjust the alkaline pH of the water layer to 8.2, extract twice with ethyl acetate (500mL*2), wash the organic layer with water, and saturated salt Washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated.

[0048] Add 200 mL of ethyl acetate, heat to dissolve, slowly cool to below 0°C, stir at the same temperature for 1 h, filter, and dry to obtain 45.8 g of the target compound (I), with a yield of 92.2% and a ...

Embodiment 3

[0050] Under nitrogen protection, compound (IV) (20.8g, 0.06mol), tributylphosphine (30.3g) and water (2.16g) were added to 1000mL acetonitrile, stirred at room temperature for 20min, and the reaction solution was cooled to -10°C , then added compound (III) (57.4 g, 0.10 mol) and tetramethylguanidine (23.6 g, 0.20 mmol) dropwise, and reacted at -10°C for 5 h after the dropwise addition.

[0051] Add 500mL of ethyl acetate and 250mL of water, adjust the aqueous solution to an acidic pH of 3.9, separate the layers, take the water layer, adjust the alkaline pH of the water layer to 8.0, extract twice with ethyl acetate (550mL*2), wash the organic layer with water, and wash with saturated salt Washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated.

[0052] Add 100mL of ethyl acetate, heat to dissolve, add dropwise 200mL of n-hexane, slowly cool to below 0°C, stir at the same temperature for 4h, filter and dry to obtain 44.8g of the target compound (I...

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Abstract

The invention discloses a preparation method for tebipenem pivoxil shown as formula 1. The preparation method comprises the following step of performing the following reaction on a compound III and a compound IV in an organic solvent and water, with the action of (R1)3P and an organic base, under inert gas protection, wherein the volume ratio of the organic solvent and water is 1000 : 1-20 : 1; a reaction temperature is -40-50 DEG C; and R1 represents phenyl or C2-C8 alkyls. The preparation method is easy to operate, simple in post-treatment, with the product having high yield and high purity, and is suitable for industrialized production.

Description

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Claims

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Application Information

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Owner SHANGHAI INST OF PHARMA IND
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