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Synthesis method of sulbactam acid

A technology of sulbactam acid and a synthesis method, applied in the field of sulbactam acid synthesis, can solve problems such as low yield, and achieve the effects of improving total yield, reducing product loss, and reducing side reactions

Inactive Publication Date: 2019-03-08
常州红太阳药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction yield of sulbactamic acid prepared by traditional techniques is generally about 70%, which is relatively low and there is still room for improvement.

Method used

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  • Synthesis method of sulbactam acid
  • Synthesis method of sulbactam acid
  • Synthesis method of sulbactam acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A kind of synthetic method of sulbactam acid, comprises the following steps:

[0043] S1, diazotization and bromination reactions, as follows:

[0044] Add 843g of ethyl acetate to No. 1 reactor, cool down to 0°C, stir at a speed of 50r / min, add 240g (1.5mol) of bromine and 420g of pure water dropwise while stirring, control the temperature at 3°C, and then 490 g (1 mol) of 20% dilute sulfuric acid was added dropwise.

[0045] Control the temperature at 4°C, stir at a speed of 250r / min, add 103.5g of solid sodium nitrite while stirring, add the solid sodium nitrite in 5 times, and add the time for 15 minutes.

[0046]Add 216g (1mol) of 6-aminopenicillanic acid into the No. 1 reaction kettle from the feeding port with a vacuum feeder, control the temperature at 25°C, keep it warm for 60min, and the reaction ends.

[0047] Add sodium bisulfite solution (750g water+375g sodium bisulfite) dropwise to No. 1 reactor, and control the temperature to 10°C to make the color of ...

Embodiment 2

[0070] A kind of synthetic method of sulbactam acid, comprises the following steps:

[0071] S1, diazotization and bromination reactions, as follows:

[0072] Add 952g of ethyl acetate to No. 1 reactor, cool down to 3°C, stir at a speed of 50r / min, add 272g (1.7mol) of bromine and 474g of pure water dropwise while stirring, control the temperature at 4°C, and then 639 g (1.5 mol) of 23% dilute sulfuric acid was added dropwise.

[0073] Control the temperature at 6°C, stir at a speed of 250r / min, add 117g of solid sodium nitrite while stirring, add the solid sodium nitrite in 5 times, and add the time for 17 minutes.

[0074] Add 216g (1mol) of 6-aminopenicillanic acid into the No. 1 reaction kettle from the feeding port with a vacuum feeder, control the temperature at 27°C, keep it warm for 60min, and the reaction ends.

[0075] Add sodium bisulfite solution (750 g of water+375 g of sodium bisulfite) dropwise to No. 1 reactor, and control the temperature to 13° C. to fade th...

Embodiment 3

[0092] A kind of synthetic method of sulbactam acid, comprises the following steps:

[0093] S1, diazotization and bromination reactions, as follows:

[0094] Add 852g of ethyl acetate to No. 1 reaction kettle, cool down to 5°C, stir at a speed of 50r / min, add bromine 320g (2mol) and pure water 430g dropwise while stirring, control the temperature at 5°C, and then drop Add 784g (2mol) of 25% dilute sulfuric acid.

[0095] Control the temperature at 8°C, stir at a speed of 250r / min, add 113.5g of solid sodium nitrite while stirring, add the solid sodium nitrite in 5 times, and add the time for 20 minutes.

[0096] Add 216g (1mol) of 6-aminopenicillanic acid into the No. 1 reaction kettle from the feeding port with a vacuum feeder, control the temperature at 30°C, keep it warm for 60min, and the reaction ends.

[0097] Add sodium bisulfite solution (750g water+375g sodium bisulfite) dropwise to No. 1 reactor, and control the temperature to 15°C to make the color of the materia...

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Abstract

The invention relates to the field of medicine synthesis and provides a synthesis method of sulbactam acid, aiming at the problem of low yield of a traditional synthesis manner. The synthesis method comprises the following steps: S1, carrying out diazotization and bromination reaction: adding bromine, a dilute sulfuric acid solution and a sodium nitrite solid into 6-aminopenicillanic acid, whereinthe concentration of the dilute sulfuric acid solution is 20 to 25 percent; reacting to obtain a first intermediate; S2, carrying out oxidization reaction: dropwise adding potassium permanganate andthe dilute sulfuric acid solution into the first intermediate, wherein the concentration of the dilute sulfuric acid solution is 20 to 25 percent; S3, carrying out hydrogenation reaction: dropwise adding zinc powder and the dilute sulfuric acid solution into a second intermediate and reacting to obtain the sulbactam acid. The dilute sulfuric acid solution with the concentration of 20 to 25 percentis used for reacting, which facilitates the improvement of the activity of the diazotization and bromination reaction and the oxidization reaction, and reactants are enabled to react more completely,so that the improvement of the yield of the diazotization and bromination reaction and the oxidization reaction is facilitated, and the total yield of the reaction is further improved.

Description

technical field [0001] The invention relates to the field of drug synthesis, more specifically, it relates to a synthesis method of sulbactam acid. Background technique [0002] Sulbactamic acid is a semi-synthetic broad-spectrum β-lactamase inhibitor. It is a competitive irreversible β-lactamase inhibitor. It has a good synergy with β-lactam antibiotics In recent years, it has been widely used in medicine. The structural formula of sulbactamic acid is shown below. [0003] [0004] Sulbactam acid is off-white or light yellow crystalline powder, easily soluble in water, alcohol and ester, but hardly soluble in ether. Sulbactam acid is the preferred enzyme inhibitor of cephalosporins and penicillins, and belongs to atypical β-lactam drugs. Due to the long-term and large-scale use of cephalosporins and penicillins, β-lactamase has produced antibiotic resistance, and sulbactam, when used in conjunction with cephalosporins and penicillins, inhibits the activity of β-lactam...

Claims

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Application Information

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IPC IPC(8): C07D499/04C07D499/18C07D499/86
CPCC07D499/04C07D499/18C07D499/86
Inventor 陈建林张雪皎
Owner 常州红太阳药业有限公司
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