A kind of preparation method of d-sulbenicillin sodium

A technology of sulfobenicillin sodium and sulfophenylacetic acid, applied in the field of pharmaceutical synthesis, can solve the problems such as the unmentioned preparation method of D-sulfophenylacetic acid triethylamine salt, unstable intermediates, non-separation of acid chlorides, etc., and achieve process stability Feasible, high product yield, easy to operate

Active Publication Date: 2020-05-29
CHENGDU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The former sulfophenylacetyl chloride is difficult to prepare, which is very inconvenient in industry, or the acid chloride is unstable, or the intermediate is unstable in the subsequent reaction, and it is corrosive to the equipment, and the acid chloride is not separated, resulting in inaccurate measurement
In the latter existing method, the preparation method of D-sulfophenylacetic acid triethylamine salt is not mentioned, and the product obtained is DL-mixture

Method used

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  • A kind of preparation method of d-sulbenicillin sodium
  • A kind of preparation method of d-sulbenicillin sodium

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Embodiment 1

[0029] The preparation of embodiment 1 D-sulfophenylacetic acid sodium salt

[0030] 100 g of D-sulfophenylacetic acid L-histidine salt (0.270 mol) was suspended in a mixed solvent of 1000 ml of acetone and 100 ml of ethanol. Add triethylamine, stir for 30 minutes, filter and recover L-histidine, add sodium isooctanoate, and stir for 1-2 hours. The solid was collected by filtration and dried under reduced pressure to obtain 45.6 g of sodium D-sulfophenylacetate.

Embodiment 2

[0031] The preparation of embodiment 2 D-sulfophenylacetic acid potassium salt

[0032] As in Example 1, potassium isooctanoate was used to replace sodium isooctanoate to obtain 47.2 grams of potassium salt of D-sulfophenylacetic acid.

Embodiment 3

[0033] The preparation of embodiment 3 D-sulfophenylacetic acid triethylamine salt

[0034] 100 g of D-sulfophenylacetic acid L-histidine salt (0.270 mol) was suspended in a mixed solvent of 1000 ml of acetone and 100 ml of ethanol. Add triethylamine, stir for 30 minutes, and filter to recover L-histidine. Add 13.0 g of formic acid. Stir for 1-2h. The solid was collected by filtration and dried under reduced pressure to obtain 76.3 g of D-sulfophenylacetic acid triethylamine salt.

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Abstract

The invention discloses a method for preparing D-sulbenicillin sodium. The method includes steps of removing L-amino acid from L-amino acid salt of D-sulfophenylacetic acid in solvents and carrying out salt forming to obtain D-sulfophenylacetic acid salt; carrying out reaction on the D-sulfophenylacetic acid salt and acylating agents to obtain mixed acid anhydride; dissolving 6-APA in organic solvents under the effect of organic alkali; dropwise adding mixed acid anhydride solution into 6-APA solution, and carrying out sufficient reaction and after-treatment to obtain the D-sulbenicillin sodium. The D-sulfophenylacetic acid is an intermediate. The 6-APA is a matrix. The method has the advantages that the D-sulbenicillin sodium is prepared by the aid of novel synthetic routes, conditions are mild, the method includes stable process and is easy to implement, and the problems of instable processes of existing methods or insufficient optical purity of products and the like can be solved bythe aid of the method.

Description

technical field [0001] The application belongs to the technical field of pharmaceutical synthesis, and in particular relates to a preparation method of D-sulfbenicillin sodium. Background technique [0002] Sulbenicillin, English name is Sulbenicillin, also known as α-sulfonate benzyl penicillin, α-sulfobenzyl penicillin, its medicinal form is sodium salt, Sulbenicillin sodium, chemical name (2S, 5R, 6R) -3,3-Dimethyl-6-(2-phenyl-2-sulfoacetamido)-7-oxo-4-thia-1-azabicyclo[3,2,0]heptane -2-Formic acid disodium salt, molecular formula C 16 h 16 N 2 Na 2 o 7 S 2 , the molecular weight is 458.42. This product is a broad-spectrum semi-synthetic penicillin. Its antibacterial spectrum is similar to that of carbenicillin. It has killing effect on Pseudomonas aeruginosa and Proteus, slightly stronger antibacterial effect on drug-resistant Staphylococcus aureus, and relatively stable on β-lactamase. After intramuscular injection, the blood concentration quickly reaches a peak...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/62
Inventor 陈林李江红苟小军颜军石克金杨晨任凤英黄啸徐明琴
Owner CHENGDU UNIV
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