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Method for reduction preparation of 4-AA with inorganic reducing agent

A reducing agent and inorganic technology, applied in the field of β-lactam drugs, can solve the problems of environmental protection pressure, large amount of wastewater discharge, and unknown mechanism, achieve significant environmental protection and economic value, reduce wastewater treatment costs, and avoid large-scale The effect of transformation

Active Publication Date: 2018-03-06
JIANGSU HANKUO BIOLOGICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In previous studies, researchers usually only focused on the screening of oxidants and oxidation conditions, and less consideration was given to the reduction part, mainly because the process and mechanism of ozone oxidation to remove N-alkyl groups are still unclear. There is no 4-AA in the ozonation reaction solution obtained after ozone oxidation, and 4-AA can only be detected after reduction. It is speculated that an intermediate-compound III may be produced during the reduction process. Compound III is reduced to obtain 4-AA, compound III The structural formula is: The structural formula of 4-AA is: Unknown mechanism makes research difficult
In actual production, the reduction part is a two-step reduction, that is, adding an excess of sodium thiosulfate solution for reduction, and then adding an excess of thiourea to continue the reduction, which leads to ammonia nitrogen (1.6wt%) in the waste water produced during the preparation of 4-AA. The content of sulfur and sulfur (8wt%) is very large, the COD value is very high (greater than 2000mg / L), the smell is strong, and the environmental protection pressure is high
The two-step reduction process in the reduction part has the largest amount of wastewater discharge in the entire 4-AA production process, which has seriously endangered environmental safety.

Method used

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  • Method for reduction preparation of 4-AA with inorganic reducing agent
  • Method for reduction preparation of 4-AA with inorganic reducing agent
  • Method for reduction preparation of 4-AA with inorganic reducing agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Put 100g of zinc powder with a mesh number of 100 in 0.5mol / L NH 4 Activate in Cl aqueous solution, stir at room temperature for 2 hours, filter, wash with distilled water until it becomes neutral, and vacuum-dry at 70°C under reduced pressure to obtain activated zinc powder for future use;

[0037] (2) Add 20.0 grams of compound I to a 250ml three-necked flask, add 150ml of methanol, stir at room temperature until clear (that is, the solution of compound I is obtained), the temperature of the system drops to -20°C, and ozone is introduced to react, and the temperature is maintained at - Between 20--15°C, TLC detects the reaction until the raw material point disappears (that is, the ozonated reaction liquid is obtained), slowly adds 35g of activated zinc powder obtained in step (1) to carry out the reduction reaction, slowly raises the temperature to 0°C, and reacts for 1.5 hours, the mixture was obtained;

[0038] (3) Filter the mixed solution obtained in step (2)...

Embodiment 2

[0042] (1) Place 100g of 80-mesh iron powder in 0.5mol / L HAc aqueous solution for activation, stir at 50°C for 2 hours, filter, wash with distilled water until it becomes neutral, and vacuum-dry at 70°C under reduced pressure to obtain activated iron powder, spare;

[0043] (2) Add 20.0 grams of compound I to a 250ml three-necked flask, add 150ml of methanol, stir at room temperature until clear (that is, the solution of compound I is obtained), the temperature of the system drops to -20°C, and ozone is introduced to react, and the temperature is maintained at - Between 20--15°C, TLC detects the reaction until the raw material point disappears (that is, the ozonated reaction solution is obtained), slowly add 23g of activated iron powder obtained in step (1) to carry out the reduction reaction, slowly raise the temperature to 0°C, and react for 2.5 hours, the mixture was obtained;

[0044] (3) Filter the mixed solution obtained in step (2), wash the filter cake with a small am...

Embodiment 3

[0048] (1) Put 80g of 100 mesh aluminum powder in 0.5mol / L NH 3 ·H 2 Activate in aqueous solution of O, stir at 50°C for 2 hours, filter, wash with distilled water until neutral, and vacuum-dry at 70°C under reduced pressure to obtain activated aluminum powder, which is ready for use;

[0049] (2) Add 20.0 grams of compound I to a 250ml three-necked flask, add 150ml of methanol, stir at room temperature until clear (that is, the solution of compound I is obtained), the temperature of the system drops to -20°C, and ozone is introduced to react, and the temperature is maintained at - Between 20--15°C, TLC detects the reaction until the raw material point disappears (that is, the ozonated reaction solution is obtained), slowly add 20g of the activated aluminum powder obtained in step (1) to carry out the reduction reaction, slowly raise the temperature to 0°C, and react for 1.5 hours, the mixture was obtained;

[0050] (3) Filter the mixed solution obtained in step (2), wash th...

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Abstract

The invention discloses a method for reduction preparation of (3R,4R)-4-acetoxyl-3-[(R)-1-[(terbutyldimethylsilyl)oxy-ethyl]-2-azetidinone with an inorganic reducing agent. The inorganic reducing agent is reductive metal powder. The method includes the following steps that firstly, the inorganic reducing agent is pretreated, wherein the reductive metal powder is placed in an acidic or alkaline solution to be activated to obtain activated metal powder; secondly, ozone is introduced into a solution of a compound I for an oxidation reaction to obtain an ozonization reaction solution; thirdly, theactivated metal powder obtained in the first step is added into the ozonization reaction solution obtained in the second step for a reduction reaction, and (3R,4R)-4-acetoxyl-3-[(R)-1-[(terbutyldimethylsilyl)oxy-ethyl]-2-azetidinone is obtained, wherein the structural formula of the compound I is shown in the description. The method only needs one-step reduction, the amount of wastewater can be reduced, the content of ammonia nitrogen and sulfur in the wastewater is reduced, and the COD value of the wastewater is reduced.

Description

technical field [0001] The present invention relates to the field of production of β-lactam drugs, especially penem antibiotics, in particular, an inorganic reducing agent for preparing penem antibiotic intermediate (3R,4R)-4-acetoxy-3 - the method of [(R)-1-tert-butyldimethylsiloxo-ethyl]-2-azetidinone (ie, 4-AA). Background technique [0002] Penem antibiotics are a class of antibiotics with the broadest antibacterial spectrum and the strongest antibacterial effect among known antibacterial drugs so far. These antibiotics can selectively bind to the penicillin-binding protein (PBP) on the bacterial membrane, so that it cannot be cross-linked, thereby causing a defect in the cell wall, causing the bacterial cell to rupture and die. Penem antibiotics have very low toxicity to human cells and have no effect on human cells within their effective antibacterial concentrations. It has ultra-broad-spectrum, long half-life, high-efficiency antibacterial activity and pharmacokinet...

Claims

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Application Information

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IPC IPC(8): C07F7/18
CPCC07F7/1804C07F7/1892
Inventor 潘庆华周熹
Owner JIANGSU HANKUO BIOLOGICAL
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