Method for purifying D (-)-sulbenicillin sodium

A technology of sulfbenicillin sodium and its purification method, which is applied in the field of purifying D-sulfbenicillin sodium with β-cyclodextrin, can solve the problems of easy racemization of the L-isomer, complex process, high equipment cost, etc., and achieve the effect of improving production efficiency

Active Publication Date: 2014-04-09
HUNAN ER KANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are certain defects in each method, such as the reaction process is difficult to control when the chiral source synthesis method is used for the production of sulbenicillin sodium, and the L-isomer in the product is easy to racemize; the asymmetric synthesis method and high-performance liquid chromatography have complex processes. , high equipment costs and other issues that cannot be applied to industry

Method used

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  • Method for purifying D (-)-sulbenicillin sodium
  • Method for purifying D (-)-sulbenicillin sodium
  • Method for purifying D (-)-sulbenicillin sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (a) the crude product of sulbenicillin sodium and water are mixed and dissolved in a weight ratio of 2:1;

[0054] (b) The temperature of the solution is kept at 30°C and passed through a porous ceramic tube with a β-cyclodextrin membrane with a pore size of 60 μm, and the solution flow rate is 6dl / sec;

[0055] (c) Add dehydrated ethanol of 1 / 2 weight of the crude product of sulbenicillin sodium and isopropanol of the weight of the crude product of sulbenicillin sodium, stir and grow crystals in the reaction tank until a large amount of crystals are precipitated, and turn on the frozen brine to cool down for 8 hours;

[0056] (d) Centrifugal separation to obtain D(-)-sulfbenicillin sodium.

[0057] The yield of sulbenicillin sodium is 60%, wherein the content of D(-)-sulbenicillin sodium is 80%. The measured optical rotation of the product is [α]D: +160°~+180°.

Embodiment 2

[0059] (a) the crude product of sulbenicillin sodium is mixed with water in a weight ratio of 9: 1;

[0060] (b) A ceramic tube with a pore size of 2 μm passing through a loaded L-lysine-β-cyclodextrin membrane at room temperature, and a solution flow rate of 2 dl / sec;

[0061] (c) Add dehydrated alcohol of 1 / 2 weight of the crude product of sulbenicillin sodium and isopropanol of the weight of the crude product of sulbenicillin sodium, stir and grow crystals in the reaction tank until a large amount of crystals are precipitated, and turn on the frozen brine to cool down for 9 hours;

[0062] (d) Centrifugal separation to obtain D(-)-sulfbenicillin sodium.

[0063] The yield of sulbenicillin sodium is 65%, wherein the content of D(-)-sulbenicillin sodium is 99%. The measured optical rotation of the product is [α]D: +175°~+180°.

[0064] NMR test results of the obtained product: 1H-NRM (400MHz, D2O) δ (ppm): 1.4025 (t, 6H, -CH3), 4.1153 (d, H, -CH-COONa), 4.9275 (s, H, Ar- C...

Embodiment 3

[0066] (a) the crude product of sulbenicillin sodium is mixed with water in a weight ratio of 7: 1;

[0067] (b) Keep the solution temperature at 27°C and pass through a ceramic tube loaded with carboxymethyl-β-cyclodextrin membrane with a pore size of 100 μm, and the solution flow rate is 10dl / sec;

[0068] (c) Add dehydrated ethanol of 1 / 2 weight of the crude product of sulbenicillin sodium and isopropanol of the weight of the crude product of sulbenicillin sodium, stir and grow crystals in the reaction tank until a large amount of crystals are precipitated, and turn on the frozen brine to cool down for 10 hours;

[0069] (d) Centrifugal separation to obtain D(-)-sulfbenicillin sodium.

[0070] The yield of sulbenicillin sodium is 50%, wherein the content of D(-)-sulbenicillin sodium is 93%. The measured optical rotation of the product is [α]D: +170°~+180°.

[0071] It can be seen from the above that the product obtained in Example 2 has the narrowest range of optical rota...

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Abstract

The invention provides a method for purifying D (-)-sulbenicillin sodium, which comprises the following steps of: mixing a sulbenicillin sodium crude product and water in a weight ratio of (1-10):1, and dissolving; allowing solution to pass through a beta-cyclodextrin membrane-loaded porous ceramic tube at the flow speed of between 1 and 10 dl / second; adding a solvent, stirring until crystals are not precipitated, and cooling at a low temperature; and centrifuging to obtain the D (-)-sulbenicillin sodium. The content of the D (-)-sulbenicillin sodium processed by the method is 99 percent, and the yield is 65 percent; and the method is simple and convenient and low in requirement on equipment, and the cost of generating the D (-)-sulbenicillin sodium is reduced effectively.

Description

technical field [0001] The invention relates to a method for purifying D(-)-sulfbenicillin sodium, in particular to a method for purifying D(-)-sulfbenicillin sodium with β-cyclodextrin. Background technique [0002] The molecular structure of sulfbenicillin sodium has chirality, so it can be divided into L-body, D-body and racemate. Industrially, the crude product of sulbenicillin sodium is a mixture of L-isomer (D(-)) and D-isomer (L(+)), and its mass ratio is about 3:1. It has been found that the biological activity of D(-)-sulfbenicillin sodium is 4 to 8 times higher than that of L(+)-sulfbenicillin sodium, so a kind of method for extracting D(-)-sulfbenicillin sodium from industrial crude products has been being sought. method. [0003] Common methods for separating chiral compounds include chiral source synthesis, asymmetric synthesis and high performance liquid chromatography. There are certain defects in each method, such as the reaction process is difficult to co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/62C07D499/18
Inventor 帅放文王向峰章家伟
Owner HUNAN ER KANG PHARMA
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