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Method for synthesizing 1-(6-nitrobenzimidazolyl)ethyl palmitate on line under catalysis of lipase

A technology of nitrobenzimidazolyl and vinyl palmitate, applied in the field of online synthesis of 1-ethyl palmitate catalyzed by lipase, can solve the problems of long reaction time, low conversion rate and selectivity, and achieve high conversion rate , shorten the reaction time, reduce the effect of reaction cost

Active Publication Date: 2015-04-29
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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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-(6-nitrobenzimidazolyl) ethyl palmitate catalyzed by lipase in a microchannel reactor on-line, aiming to find an efficient and environmentally friendly On-line controllable and selective synthesis of 1-(6-nitrobenzimidazolyl) ethyl palmitate

Method used

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  • Method for synthesizing 1-(6-nitrobenzimidazolyl)ethyl palmitate on line under catalysis of lipase
  • Method for synthesizing 1-(6-nitrobenzimidazolyl)ethyl palmitate on line under catalysis of lipase
  • Method for synthesizing 1-(6-nitrobenzimidazolyl)ethyl palmitate 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-(6-nitrobenzimidazolyl) ethyl palmitate

[0033]

[0034] device reference figure 1 : 6-nitro-benzimidazole (1.0mmol) was dissolved in 10mL DMSO, vinyl palmitate (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 solution 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 wit...

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]

[0044] 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-(6-nitrobenzimidazolyl)ethyl palmitate in the microfluidic microchannel reactor of the present invention is 50°C.

Embodiment 5-8

[0046] Change the substrate molar ratio of vinyl palmitate and 6-nitro-benzimidazole 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 6-nitro-benzimidazole is constant, changes the consumption of vinyl palmitate into 1.0mmol (embodiment 5), 2.0mmol ( Example 6), 4.0mmol (Example 7), 8.0mmol (Example 8), were dissolved in 10mLDMSO respectively, and others were the same as in Example 1. The results are shown in Table 2.

[0047] Table 2: Effect of 6-nitro-benzimidazole and vinyl palmitate substrate molar ratio on reaction

[0048]

[0049] The result of table 2 shows, along with the increase of reactant vinyl palmitate, the conversion rate of reaction also increases thereupon, and when substrate ratio is 6:1, the conversion rate of reaction is optimum, and 6-nitro-benzo Essentially 72% of the imidazole has been converted to 1-(6-nitrobenzimidazolyl)ethyl palmitate. Now ...

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Abstract

The invention discloses a method for synthesizing 1-(6-nitrobenzimidazolyl)ethyl palmitate on line under the catalysis of lipase. The method comprises the steps of with 6-nitro-benzimidazole and vinyl palmitate which are in the molar 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-(6-nitrobenzimidazolyl)ethyl palmitate. 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-(6-nitrobenzimidazolyl) ethyl palmitate 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 re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/10
Inventor 杜理华杨文俊凌慧敏何锋罗锡平
Owner ZHEJIANG UNIV OF TECH
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