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Faropenem sodium preparation method

A synthesis method and intermediate technology are applied in the field of preparation of faropenem sodium, and can solve the problems of difficulty in realizing large-scale industrial production of faropenem sodium, low yield of faropenem sodium, long process route, etc., and the reaction conditions are easy to realize, The effect of high yield and strong controllability

Active Publication Date: 2007-05-09
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method of faropenem sodium reported in the above patent has a long process route, and all intermediates need to be purified, resulting in generally low yield and high cost of faropenem sodium
The above conditions make it difficult to realize large-scale industrial production of faropenem sodium

Method used

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Experimental program
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Effect test

Embodiment 1

[0025] Add 240g (R)-tetrahydrofuran-2-thioformic acid and 490g 4-AA into a 2000mL three-neck flask, add 1200mL ethyl acetate to it, and slowly add about 400mL 4N NaOH dropwise after dissolving to adjust the pH to 12-13 , and the reaction was stirred until the reaction was complete. Extract with 1500 mL ethyl acetate, collect the organic phase, wash with brine, and dry over anhydrous sodium sulfate. The condensate (440 g of colorless viscous liquid) was obtained by spin-drying under reduced pressure, which was directly used in the next step.

Embodiment 2

[0027] The condensate obtained in Example 1 was dissolved in 2000mL of dichloromethane, placed in a 3000mL three-necked flask, and 453.0mL of pyridine was added, cooled to 0°C in an ice-water bath, and 350g of allyloxyfen was added dropwise at 5-15°C A mixture of acid chloride and 350 mL of dichloromethane. After the dropwise addition is complete, continue to react under this condition for about 30 minutes. The plate layer monitors that the reaction is complete. Add 1500mL of deionized water, and the organic phase is washed with 1500mL of deionized water, 1500mL of saturated sodium bicarbonate solution, and then washed with 1500mL of saturated brine. Dry over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the condensate (580 g of colorless solid), which was set aside.

Embodiment 3

[0029] Dissolve 250 g of the solid obtained in Example 2 in 6000 mL of xylene, add 25 g of triethylamine, add it to a 10000 mL three-necked flask, stir mechanically, heat to reflux with an electric heating mantle, and add 655 mL of triethyl phosphite dropwise, about 120 Minutes dropwise completed. Heat preservation and reflux reaction for 16 hours, and concentrate under reduced pressure to obtain the ring compound (yellow solid 170 g), which is set aside.

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Abstract

The invention discloses a process for preparing Faropenem by using 4-AA as the raw material through a 'one-pot' operation, wherein the intermediates can be used directly for the next step reaction without the need for purification. The method has the advantages of low cost, high yield, and easy reaction conditions.

Description

technical field [0001] The present invention relates to faropenem sodium {5R-(3R, 6R)-6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furyl) 4-thio-1-azabicyclo[ 3.2.0] Preparation method of sodium hept-2-ene-2-carboxylate}. Background technique [0002] Faropenem Sodium (Faropenem Sodium) is 5R-(3R,6R)-6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furyl)-4-thio-1-aza Generic name for sodium bicyclo[3.2.0]hept-2-ene-2-carboxylate, whose structural formula is: [0003] [0004] Faropenem sodium is a β-lactam antibiotic of the penem class. It was developed by Suntory Company of Japan. It was first launched in Japan in 2000. It is the first drug of this type that is stable to β-lactamase and can be taken orally. Injectable broad-spectrum antibiotics. Like other β-lactam antibiotics, faropenem plays a bactericidal effect by inhibiting the synthesis of bacterial cell walls, and is suitable for patients with different degrees of infection. Its efficacy and safety have been fully affirm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/893
Inventor 赵志全彭立增李伟
Owner LUNAN PHARMA GROUP CORPORATION
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