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A synthesis process and device for (3r,4r)-4-acetoxy-3-[(r)-1-tert-butyldimethylsiloxyethyl]-2-azetidinone

A technology of tert-butyldimethylsiloxyethyl and azetidinone, which is applied in the fields of compounds of Group 4/14 elements of the periodic table, production of bulk chemicals, chemical instruments and methods, etc., can solve the problem of operational safety problems such as poor performance, low yield, and long reaction time, to achieve the effects of high safety, large heat exchange area, and improved utilization

Active Publication Date: 2018-07-17
SHANGHAI INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to solve the technical problems such as long reaction time, low yield and poor operation safety in the industrial production of 4-AA, the object of the present invention is to provide a new (3R, 4R)-4-acetoxy-3-[(R )-1-tert-butyldimethylsiloxyethyl]-2-azetidinone synthesis technique and device; the present invention synthesizes 4-AA industrial products through the continuous reaction of series loop reactors, and the adopted series loop The reactor structure is simple, the reaction time of the synthesis process is short, the operation is safe, and the product yield is high

Method used

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  • A synthesis process and device for (3r,4r)-4-acetoxy-3-[(r)-1-tert-butyldimethylsiloxyethyl]-2-azetidinone
  • A synthesis process and device for (3r,4r)-4-acetoxy-3-[(r)-1-tert-butyldimethylsiloxyethyl]-2-azetidinone

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Experimental program
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Effect test

Embodiment 1

[0033] The new 4-AA synthesis process involves the continuous reaction process using series loop reactors. Including the following steps:

[0034] (1) Put 1 part (mass) of raw material (3R, 4R)-3-[(R)-1-tert-butyldimethylsiloxyethyl)-4-acetoxy-1-( 4-Methoxyphenyl)-2-azetidinone was dissolved in 3 parts (mass) of methanol solvent under stirring at room temperature, and frozen to -10°C.

[0035] (2) A 4-series loop reactor with a single reactor volume of 200 liters (see attached figure 1 ) All reactor jackets and coils are fed with chilled brine at -25°C to -35°C, and the external circulation heat exchangers of the first and second reactors are fed with chilled brine at -25°C to -35°C.

[0036] (3) The reaction raw materials of step (1) are pumped into the first reactor with a pump. The feed volume flow rate of the raw materials is 100 liters per hour, that is, the average residence time of the reaction is 8 hours, and the circulation flow rate of each circulating pump is 12 cubic me...

Embodiment 2

[0042] 4-AA synthesis new technology, which involves the continuous reaction technology using series loop reactors. Including the following steps:

[0043] (1) Put 1 part (mass) of raw material (3R, 4R)-3-[(R)-1-tert-butyldimethylsiloxyethyl)-4-acetoxy-1-( 4-Methoxyphenyl)-2-azetidinone was dissolved in 10 parts (mass) of methanol solvent under stirring at room temperature, and frozen to -10°C.

[0044] (2) A 4-series loop reactor with a single reactor volume of 200 liters (see attached figure 1 ) All reactor jackets and coils are fed with chilled brine at -25°C to -35°C, and the external circulation heat exchangers of the first and second reactors are fed with chilled brine at -25°C to -35°C.

[0045] (3) The reaction raw materials of step (1) are pumped into the first reactor with a pump. The feed volume flow rate of the raw materials per hour is 200 liters, that is, the average residence time of the reaction is 4 hours, and the circulation flow rate of each circulating pump is 6...

Embodiment 3

[0051] 4-AA synthesis new technology, which involves the continuous reaction technology using series loop reactors. Including the following steps:

[0052] (1) Put 1 part (mass) of raw material (3R, 4R)-3-[(R)-1-tert-butyldimethylsiloxyethyl)-4-acetoxy-1-( 4-Methoxyphenyl)-2-azetidinone was dissolved in 10 parts (mass) of methanol solvent under stirring at room temperature, and frozen to -10°C.

[0053] (2) A 4-series loop reactor with a single reactor volume of 200 liters (see attached figure 1 ) All reactor jackets and coils are fed with chilled brine at -25°C to -35°C, and the external circulation heat exchangers of the first and second reactors are fed with chilled brine at -25°C to -35°C.

[0054] (3) The reaction raw materials of step (1) are pumped into the first reactor with a pump. The feed volume flow rate of the raw materials is 160 liters per hour, that is, the average residence time of the reaction is 6 hours, and the circulation flow rate of each circulating pump is 1...

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Abstract

The invention discloses a process and a device for synthesizing (3R, 4R)-4-acetoxyl-3-[(R)-1-tert-butyl dimethyl silica ethyl]-2-azetidinone. 4-AA industrial products can be synthesized by the aid of continuous reaction technologies for series connection circuit reactors. The process includes dissolving a raw material (3R, 4R)-3-[(R)-1-tert-butyl dimethyl silica ethyl]-4-acetoxyl-1-(4-methoxy phenyl)-2-azetidinone by the aid of methanol; allowing series connection circuit reaction devices to carry out oxidation deprotection on PMP protecting groups in the raw material by the aid of ozone; carrying out reduced-pressure distillation to remove the methanol and then adding water to the raw material to obtain 4-AA crude products; re-crystallizing the crude products to obtain 4-AA products. The process and the device have the advantages that the process is simple, safe in oxidation deprotection reaction operation, short in reaction time and low in running cost; the reaction yield can be greatly increased, and the mass yield of the 4-AA products is higher than 69%.

Description

Technical field [0001] The invention relates to a new synthesis technology of 4-AA products, which relates to the use of serial loop reactor continuous reaction technology to synthesize 4-AA industrial products. Background technique [0002] The chemical name of 4-AA is (3R,4R)-4-acetoxy-3-[(R)-1-tert-butyldimethylsiloxyethyl]-2-azetidinone, and its structure is A β-lactam ring containing three adjacent chiral centers. Related research has shown that the β-lactam ring is the key active center of β-lactam antibiotics. As a universal chiral synthon widely used in the synthesis of various β-lactam antibiotics, 4-AA is a very important pharmaceutical chemical and the key to the synthesis of the parent ring of penicillene and carbapenem antibiotics. The starting material is mainly used to synthesize various penem antibiotics, such as imipenem, biapenem, meropenem and faropenem. These drugs have a wide range of uses, and have spectrally powerful antibacterial effects on gram-negative...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18
CPCY02P20/55
Inventor 毛海舫赵飞飞孙揭阳赵国标陈方琪徐建忠王朝阳姚跃良章平毅敖燕胡玲
Owner SHANGHAI INST OF TECH
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