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Synthetic method of faropenem sodium

A technology of faropenem sodium and its synthesis method, which is applied in the field of organic chemical industry or pharmaceutical chemical industry, can solve the problems of inconvenient production operation and long reaction steps, and achieve the effect of easy operation

Inactive Publication Date: 2009-11-25
CHENGDU QIAOFENG TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although this method does not use expensive silver salt as a condensing agent, it needs to make R-tetrahydrofuran-2-carboxylic acid into mercapto acid in advance, so the reaction steps are longer and the actual production operation is inconvenient

Method used

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  • Synthetic method of faropenem sodium
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  • Synthetic method of faropenem sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: (3R, 4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[(R)-tetrahydrofuran-2-formylthio]nitroheterocycle Synthesis of Butan-2-one (I)

[0025] Dissolve 43.0g (0.120mol) of trityl R-tetrahydrofuran-2-carboxylate and 28.7g (0.10mol) of 4-AA in 100ml of anhydrous tetrahydrofuran, add 7.9g (0.120mol) of sodium sulfide after dissolution, and then add 24g (0.18mol) of anhydrous aluminum trichloride and 10ml of boron trifluoride / diethyl ether solution, stirred and reacted at 40°C for 24 hours, after the reaction was detected by TLC, the reaction solution was cooled to 0°C, and 100ml of saturated sodium bicarbonate was slowly added dropwise Solution, keep the temperature not exceeding 10°C. After the dropwise addition, control the temperature of the water bath to not exceed 40°C to remove tetrahydrofuran by distillation under reduced pressure, add 200ml ethyl acetate to the residue, filter out the solid, separate the organic phase from the filtrate, and then use 100ml...

Embodiment 2

[0026] Example 2: (3R, 4R)-1-allyloxyoxalyl-3-[(R)-1-tert-butyldimethylsiloxyethyl]-4-[(R)-tetrahydrofuran- Synthesis of 2-formylthio]azetidin-2-one (II)

[0027] Dissolve 22.0g (0.061mol) of intermediate I in 100ml of dry dichloromethane, cool to 0°C and dropwise add 14.6g (0.098mol) of allyloxy oxalyl chloride. After the addition is complete, add 14.5 ml of triethylamine, after the addition, keep at 0-5°C for 2 hours. After the reaction is detected by TLC, add 100ml of water to the reaction solution and stir, then remove the water phase, and then use 50ml of saturated sodium bicarbonate solution, 50ml of water, and 50ml of saturated Washed with brine, dried over anhydrous magnesium sulfate and evaporated to dryness to obtain Compound II as a colorless oil, weighing 25.6 g.

Embodiment 3

[0028] Example 3: (5R, 6S)-6-[(R)-1-tert-butyldimethylsiloxyethyl]-2-[(R)-tetrahydrofuran-2-formylthio]penem -Synthesis of propenyl 3-carboxylate (III)

[0029] Dissolve 13g (0.0276mol) of intermediate II in 20ml of xylene, add 11.5g (0.069mol) of triethyl phosphite and 50mg of hydroquinone, reflux for 2 hours, wash the reaction solution with water, dry and evaporate to dryness to obtain Yellow oil, the yellow oil was recrystallized from ethyl acetate / petroleum ether to obtain compound III as a yellow solid with a weight of 7.6 g.

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Abstract

The invention discloses a synthetic method of faropenem sodium. The method uses (3R,4R)-3-[(R)-1-tert-butyldiemthylsilyloxyethyl]-4-[(R)-acetoxyl]azetidin-2-one (4-AA) as raw material and prepares the faropenem sodium through a five-step reaction. The method does not use a silver salt as a condensing agent, does not use 4-tetrahydrofuran-2-formic acid which is previously made into mercaptan acid, has simple and convenient operation, and is suitable for industrial production. The product purity and the total yield all exceed the prior art.

Description

Technical field: [0001] The invention relates to a method for synthesizing faropenem sodium, which belongs to the field of organic chemical industry or pharmaceutical chemical industry. Background technique: [0002] The chemical name of Faropenem Sodium is 5R-(3R,6R)-6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furyl)-4-sulfur-1- Sodium azabicyclo[3.2.0]hept-2-ene-2-carboxylate 2.5 times hydrate, its structural formula is as follows: [0003] [0004] Faropenem sodium belongs to carbapenem β-lactam antibiotics. Since a tetrahydrofuran group is attached to the 2-position of the carbapenem parent ring, it is chemically stable and relatively stable to β-lactamase. Faropenem sodium has strong antibacterial activity against aerobic and anaerobic Gram-positive bacteria and negative bacteria, and can be injected or taken orally. [0005] The synthetic method of faropenem sodium mainly contains following several kinds at present: [0006] 1. Chinese Patent Publication No. CN18878...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/893C07D499/16A61P31/04
CPCY02P20/55
Inventor 黎鹏杨军王勇潘野廖文武
Owner CHENGDU QIAOFENG TECH DEV
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