Faropenem sodium preparation method

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

Active Publication Date: 2006-02-15
LUNAN PHARMA GROUP CORPORATION
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  • Abstract
  • Description
  • Claims
  • Application Information

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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 g

Method used

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Example Embodiment

[0024] Example 1:

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

Example Embodiment

[0026] Example 2:

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

Example Embodiment

[0028] Example 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 The minute addition is complete. The reaction was kept under reflux for 16 hours, and concentrated under reduced pressure to obtain the cyclized compound (yellow solid 170g), which was used for later use.

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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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IPC IPC(8): C07D499/893
Inventor 赵志全彭立增李伟
Owner LUNAN PHARMA GROUP CORPORATION
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