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Method for synthesizing 1-(4-nitroimidazolyl)ethyl laurate on line under catalysis of lipase

A technology of nitroimidazole base and vinyl laurate, which is applied in the field of lipase-catalyzed online synthesis of 1-ethyl laurate, can solve the problems of low conversion rate and selectivity, long reaction time, etc., and achieve shortened reaction time, Effect of high conversion rate and reduction of reaction cost

Active Publication Date: 2015-04-29
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] At present, many domestic and foreign scholars have studied the enzyme-catalyzed synthesis of Markovnikov addition reaction in organic media, but this method mostly uses acylase for catalysis, which often requires a long reaction time (24-96h), and The conversion rate and selectivity of the reaction are not high, so we studied the method of synthesizing 1-(4-nitroimidazolyl) ethyl laurate on-line catalyzed by lipase in a microchannel reactor, aiming to find an efficient and environmentally friendly lauric acid On-line Controllable and Selective Synthesis of Ethyl Acid 1-(4-Nitroimidazolyl) Ester

Method used

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  • Method for synthesizing 1-(4-nitroimidazolyl)ethyl laurate on line under catalysis of lipase
  • Method for synthesizing 1-(4-nitroimidazolyl)ethyl laurate on line under catalysis of lipase
  • Method for synthesizing 1-(4-nitroimidazolyl)ethyl laurate on line under catalysis of lipase

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]Embodiment 1: the synthesis of 1-(4-nitroimidazolyl) ethyl laurate

[0033]

[0034] device reference figure 1 : 4-nitro-imidazole (1.0mmol) was dissolved in 10mL DMSO, vinyl laurate (6.0mmol) was dissolved in 10mL DMSO, and then filled in two 10mL syringes for use. 0.87g of lipase Lipozyme TLIM was evenly filled in the reaction channel, driven by the PHD2000 syringe pump, the two reaction solutions were separated at 10.4 μL min -1 The flow rate enters the reaction channel through the Y-shaped interface for reaction, and the temperature of the reactor is controlled at 50°C through a water bath thermostat. The reaction solution flows continuously in the reaction channel for 30 minutes, and the reaction results are tracked and detected by thin-layer chromatography (TLC).

[0035] The reaction liquid was collected online by the product collector, and the solvent was distilled off under reduced pressure to obtain the crude product, which was wet-packed with 200-300 mesh ...

Embodiment 2-4

[0040] Change the temperature of the microfluidic channel reactor, others are the same as in Example 1, and the reaction results are as shown in Table 1:

[0041] Table 1: Effect of Temperature on Reaction

[0042]

[0043] The results in Table 1 show that when the flow rate is 10.4 μL min -1 , when the reaction time is 30min, the conversion rate increases significantly with the increase of the reaction temperature. When the reaction temperature reaches 50°C, the conversion rate of the reaction is the best. If the temperature continues to rise at this time, the enzyme activity will decrease. , thereby causing the conversion rate of the reaction to decrease, so the optimal reaction temperature of 1-(4-nitroimidazolyl)ethyl laurate in the microfluidic microchannel reactor of the present invention is 50°C.

Embodiment 5-8

[0045] Change the substrate molar ratio of vinyl laurate and 4-nitro-imidazole in the microfluidic microchannel reactor to be 1:1 (embodiment 5), 2:1 (embodiment 6), 4:1 (embodiment 7), 8:1 (embodiment 8), the consumption 1.0mmol of 4-nitro-imidazole is constant, changes the consumption of vinyl laurate into 1.0mmol (embodiment 5), 2.0mmol (embodiment 6) respectively .

[0046] Table 2: Effect of 4-nitro-imidazole and vinyl laurate substrate molar ratio on reaction

[0047]

[0048] The result of table 2 shows, along with the increase of reactant vinyl laurate, the conversion ratio of reaction also increases thereupon, and when substrate ratio is 6:1, the conversion ratio of reaction is optimum, and 4-nitro-imidazole is basic There has been quantitative complete conversion to 1-(4-nitroimidazolyl)ethyl laurate. Now if continue to increase the consumption of reactant vinyl laurate, will cause the conversion efficiency of reaction to reduce, thereby, the optimal substrate r...

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Abstract

The invention discloses a method for synthesizing 1-(4-nitroimidazolyl)ethyl laurate on line under the catalysis of lipase. The method comprises the steps of with 4-nitro-imidazole and vinyl laurate which are in the mass ratio of 1:(1-8) as raw materials, 0.5-1.0g of lipase Lipozyme TLIM as a catalyst and a DMSO solvent as a reaction solvent, uniformly filling a reaction channel of a microfluidic channel reactor with the lipase Lipozyme TLIM, wherein the internal diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4mm, and the reaction channel is 0.5-1.0m long; and continuously introducing the raw materials and the reaction solvent to the reaction channel to carry out Markovnikov addition reaction, controlling the reaction temperature at 40-55 DEG C and the reaction time at 20-35 minutes, collecting a reaction solution on line, and carrying out conventional treatment on the reaction solution to obtain 1-(4-nitroimidazolyl)ethyl laurate. The method has the advantages of short reaction time, high selectivity and high yield.

Description

(1) Technical field [0001] The invention relates to a lipase-catalyzed method for synthesizing 1-(4-nitroimidazolyl)ethyl laurate on-line. (2) Background technology [0002] Markovnikov addition is one of the important tools for forming C-C, C-N, C-O, and C-X bonds, and is a very important addition reaction in organic synthesis. Nitrogen heterocyclic compounds are used as addition substrates not only because such compounds are good nucleophilic addition reagents, but also because imidazole derivatives generally have high pharmacological activity and are important drug intermediates. [0003] The chemical method of Markovnikov addition generally reacts quickly and has a high conversion rate, but its harsh reaction conditions will cause certain environmental pollution and energy waste, and many side reactions are associated with it, which seriously affects the yield and selectivity of the addition. Due to the advantages of high selectivity, mild conditions, and fast reaction ...

Claims

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Application Information

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IPC IPC(8): C12P17/10
Inventor 杜理华徐亮亮杨文俊成柄灼凌慧敏何锋罗锡平
Owner ZHEJIANG UNIV OF TECH
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