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Method for synthesizing carbenicillin sodium pharmaceutical intermediate diethyl(phenylmethylene)malonate

A technology of diethyl benzylidene malonate and carbenicillin sodium, which is applied in the field of synthesis of diethyl benzylidene malonate, a pharmaceutical intermediate of carbenicillin sodium, can solve the problems of weakened antibacterial activity, etc. Achieve the effects of reducing intermediate links, reducing reaction temperature and reaction time, and increasing reaction yield

Inactive Publication Date: 2016-05-11
CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Infusion of this product and aminoglycoside antibiotics in the same bottle can significantly weaken the antibacterial activity of both

Method used

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  • Method for synthesizing carbenicillin sodium pharmaceutical intermediate diethyl(phenylmethylene)malonate

Examples

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Effect test

example 1

[0013] Add 1.3mol of diethyl malonate (3) in the reaction vessel, the mass fraction is 70% benzylamine alcohol solution 1.6mol, the mass fraction is 40% cyclohexane 500ml, aluminum oxide 1.5mol, the mass fraction is 60% Toluene 200ml, raise the solution temperature to 80°C, reflux for 5h, lower the solution temperature to 60°C, continue the reaction for 80min, lower the solution temperature to 10°C, let stand for 2h, separate the solution, take out the oil layer, the mass fraction is 35% oxalic acid solution Washing, washing with potassium sulfite solution, extracting 5 times with a xylene solution with a mass fraction of 85%, combining the extracts, dehydrating phosphorus pentoxide, and distilling under reduced pressure at 0.3kPa to collect fractions at 110--117°C. Recrystallized in 91% acetonitrile to obtain 267.59 g of crystalline diethyl benzylidene malonate with a yield of 83%.

example 2

[0015] Add 1.3mol of diethyl malonate (3) in the reaction vessel, the mass fraction is 72% benzylamine alcohol solution 1.7mol, the mass fraction is 42% cyclohexane 500ml, aluminum oxide 1.5mol, the mass fraction is 62% Toluene 200ml, raise the solution temperature to 82°C, reflux for 6h, lower the solution temperature to 63°C, continue the reaction for 92min, lower the solution temperature to 12°C, let stand for 3h, separate the solution, take out the oil layer, the mass fraction is 38% oxalic acid solution Washing, washing with potassium sulfite solution, extracting 6 times with a mass fraction of 83% xylene solution, combining the extracts, dehydrating with anhydrous potassium carbonate, and distilling under reduced pressure at 0.31kPa to collect fractions at 110--117°C. Recrystallized in 93% acetonitrile to obtain 277.26 g of crystalline diethyl benzylidene malonate with a yield of 86%.

example 3

[0017] Add 1.3mol of diethyl malonate (3) in the reaction vessel, the mass fraction is 75% benzylamine alcohol solution 1.9mol, the mass fraction is 45% cyclohexane 500ml, aluminum oxide 1.5mol, the mass fraction is 65% Toluene 200ml, raise the solution temperature to 85°C, reflux for 8h, lower the solution temperature to 65°C, continue the reaction for 110min, lower the solution temperature to 17°C, let stand for 5h, separate the solution, take out the oil layer, the mass fraction is 40% oxalic acid solution Washing, washing with potassium sulfite solution, extracting 7 times with a mass fraction of 90% xylene solution, combining the extracts, dehydrating phosphorus pentoxide, and distilling under reduced pressure at 0.32kPa to collect fractions at 110--117°C. Recrystallized in 97% acetonitrile to obtain 293.38 g of crystalline diethyl benzylidene malonate with a yield of 91%.

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Abstract

A method for synthesizing a carbenicillin sodium pharmaceutical intermediate diethyl(phenylmethylene)malonate comprises the following steps: adding 1.3 mol of diethyl malonate, 1.6-1.9 mol of a phenylmethylamine alcohol solution, 500 ml of cyclohexane, 1.5 mol of alumina and 200 ml of toluene into a reaction vessel, increasing the solution temperature to 80-85 DEG C, and carrying out reflux for 5-8 h; reducing the solution temperature to 60-65 DEG C, and continuing to carry out a reaction for 80-110 min; reducing the solution temperature to 10-17 DEG C, and allowing to stand for 2-5 h; layering the solution, taking out an oil layer, washing with an oxalic acid solution, washing with a potassium sulfite solution, and extracting for 5-7 times with a xylene solution; and merging the extract liquids, dehydrating with a dehydration agent, carrying out reduced pressure distillation, collecting a 110-117 DEG C fraction, recrystallizing in acetonitrile, and thus obtaining the crystal diethyl(phenylmethylene)malonate.

Description

technical field [0001] The invention relates to a method for synthesizing carbenicillin sodium pharmaceutical intermediate benzylidene malonate diethyl ester. Background technique [0002] Carbenicillin sodium can be used for systemic infections caused by other sensitive Enterobacter species. The effect on Gram-positive bacteria is similar to ampicillin but slightly weaker. Enterococci are less sensitive to this product. Ineffective against enzyme-producing Staphylococcus aureus. The antibacterial spectrum against Gram-negative bacteria is wider than that of ampicillin, including Pseudomonas aeruginosa, indole-positive Proteus, some Serratia, some Enterobacter, and some Bacteroides. However, most strains of Pseudomonas aeruginosa have poor sensitivity to this product, and this product has a reliable antibacterial effect only at high concentrations. It also has a certain effect on anaerobic bacteria. Oral non-absorption: intravenous injection of 5g, serum drug concentrat...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/618
CPCC07C67/343
Inventor 关艮安
Owner CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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