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New technique for catalytic synthesis of AE active ester

A new technology, active ester technology, applied in the production process field of key intermediate - AE-active ester, can solve the problems of mild production and operation conditions, achieve the effect of mild production and operation conditions, reduce operation intensity, and reduce operation difficulty

Active Publication Date: 2008-01-02
SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to provide a new process for catalytically synthesizing AE-active ester, which overcomes the adverse effect of the presence of moisture on the reaction in the existing process, and introduces pyridine with high water absorption as a catalyst to promote the reaction to the positive direction conduct
The invention also solves the problem that the production operation conditions are relatively mild

Method used

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  • New technique for catalytic synthesis of AE active ester
  • New technique for catalytic synthesis of AE active ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Raw material ratio: 200 kg of aminothioxamic acid

[0022] Dibenzothiazole disulfide 250 kg

[0023] Pyridine 1.5 kg

[0024] Mixed solvent 1600 liters

[0025] Wherein the volume ratio of mixed solvent acetonitrile and dichloromethane is acetonitrile: dichloromethane=0.9:1

[0026] Triethylamine 80 kg

[0027] Phosphite triethyl ester 160 kg

[0028] 200 liters of mixed solvent in the rinse mother liquor

[0029] New acetonitrile 100 liters

[0030] New dichloromethane 200 liters

[0031] (1) Preparation of mixed solvent

[0032] Add 1,100 liters of new dichloromethane and 1,000 liters of new acetonitrile into a 3,000-liter well-sealed reactor, add 120 kg of phosphorus pentoxide under nitrogen protection, seal the reactor, heat up and distill, and collect at 80-110°C The distillate is placed in a dry and airtight storage tank for later use.

[0033] (2) Reaction

[0034] In the reaction kettle, first add 1600 liters of distilled mixed solvent, then add aminot...

Embodiment 2

[0038] Embodiment 2: according to the technique of embodiment 1, the proportioning of different raw materials is:

[0039] Aminothioxamic acid 200kg

[0040] Dibenzothiazole disulfide 250 kg

[0041] Pyridine 1 kg

[0042] Mixed solvent 1500 liters

[0043] Wherein the volume ratio of mixed solvent acetonitrile and dichloromethane is acetonitrile: dichloromethane=1.0:1

[0044] Triethylamine 82 kg

[0045] Phosphite triethyl ester 162 kg

[0046] The product yield is 91%.

Embodiment 3

[0047] Embodiment 3: according to the technique of embodiment 1, the proportioning of different raw materials is:

[0048] Aminothioxamic acid 200kg

[0049] Dibenzothiazole disulfide 255 kg

[0050] Pyridine 2 kg

[0051] Mixed solvent 1700 liters

[0052] Wherein the volume ratio of mixed solvent acetonitrile and dichloromethane is acetonitrile: dichloromethane=1.0:1

[0053] Triethylamine 80 kg

[0054] Phosphite triethyl ester 158 kg

[0055] The product yield is 91.5%.

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Abstract

The invention discloses a new technology for synthesizing AE-active ester with accelerant, which is made by condensation reaction in the triethyl phosphate and triethylamine solvent. The invention is characterized by the following: introducing pyridine with high hydroscopicity as the accelerant in order to accelerate the reaction proceeding according to the forward direction based on the original technology; changing the reaction solvent system (the mixed solvent which is comprised by acetonitrile and carrene according to (0.9-1.0):1); avoiding the problem of water content which is introduced by the new solvent; improving the normal reaction temperature; reducing the operation difficult; reducing the strength; improving the product efficient to more than 92%. The invention also achieves the recycling of the solvent by distillation.

Description

technical field [0001] The invention belongs to the field of pharmaceutical fine chemicals, and particularly relates to the production process of AE-active ester, a key intermediate for the production of cephalosporin antibiotic products. Background technique [0002] AE-active ester, English abbreviation MAEM, also known as aminothioxime active thioester, mercapto heterocyclic active ester, chemical name 2-methoxyimino-2-(2-amino-4thiazolyl)-(z)-sulfur Benzothiazolyl acetate, the molecular formula is C 13 h 10 S 3 N 4 o 2 , the structural formula is: [0003] [0004] The molecular weight is 350, and it is pale yellow needle-like crystal. It is an important raw material for the manufacture of cephalosporin antibiotics such as ceftriaxone, ceftazime, cefotaxime sodium and cefodizime. The CA registration number is N080765-85-0. Its melting point is between 128 and 130 ° C, low toxicity and slightly bitter taste, it can burn when exposed to open flames, easily solubl...

Claims

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Application Information

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IPC IPC(8): C07D277/74B01J31/02
Inventor 郑庚修刘承平候乐伟徐立臣刘先刚
Owner SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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