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Process and device for synthesizing (3R, 4R)-4-acetoxyl-3-[(R)-1-tert-butyl dimethyl silica ethyl]-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, bulk chemical production, chemical instruments and methods, etc., and can solve the problem of reaction time Long, low yield, poor operating safety and other problems, to achieve the effect of improving utilization rate, large heat exchange area and high safety

Active Publication Date: 2016-10-12
SHANGHAI APPLIED TECHNOLOGIES COLLEGE +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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  • Process and device for synthesizing (3R, 4R)-4-acetoxyl-3-[(R)-1-tert-butyl dimethyl silica ethyl]-2-azetidinone

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Embodiment 1

[0033] A new process for the synthesis of 4-AA, which involves a 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 stirred and dissolved in 3 parts (mass) of methanol solvent at room temperature, and frozen to -10°C.

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

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

Embodiment 2

[0042] A new technology for the synthesis of 4-AA, which involves the continuous reaction technology of 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 stirred and dissolved in 10 parts (mass) of methanol solvent at room temperature, and frozen to -10°C.

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

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

Embodiment 3

[0051] A new technology for the synthesis of 4-AA, which involves the continuous reaction technology of 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 stirred and dissolved in 10 parts (mass) of methanol solvent at room temperature, and frozen to -10°C.

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

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

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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 synthesis of 4-AA industrial products by adopting the continuous reaction technology of series loop reactors. 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 studies have shown that the β-lactam ring is the key active center of β-lactam antibiotics. As a general-purpose chiral synthon widely used in the synthesis of various β-lactam antibiotics, 4-AA is a very important pharmaceutical chemical and is the key starting point for the synthesis of carbapenem and carbapenem antibiotic parent rings. The raw material is mainly used for the synthesis of various penem antibiotics, such as imipenem, biapenem, meropenem and faropenem. These drugs have a wide range of uses, and have strong antibacterial e...

Claims

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Application Information

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IPC IPC(8): C07F7/18
CPCY02P20/55C07F7/1804C07F7/1892
Inventor 毛海舫赵飞飞孙揭阳赵国标陈方琪徐建总王朝阳姚跃良章平毅敖燕胡玲
Owner SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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