Method for continuously preparing benzoxazine rifamycin

A technology for rifamycin and benzoxazine, which is applied in the field of continuous preparation of benzoxazine-rifamycin, can solve the problems of low reaction yield, poor operation stability, large amount of solvent and the like, achieves high yield, Improved process efficiency and excellent mixing results

Inactive Publication Date: 2020-01-14
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The above-mentioned benzoxazine rifamycin synthesis technology has problems such as l

Method used

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  • Method for continuously preparing benzoxazine rifamycin

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Experimental program
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Effect test

Embodiment 1

[0025] Use N,N-dimethylformamide as solvent to prepare 0.394M rifamycin S solution 1 and 1.362M dimethylol-tert-butylamine solution 2, and both materials pass through the metering pump 3 and metered at a flow rate of 0.3mL / min. The pump 4 is transported to the micro-mixer 16 through two-way ball valves 7, 8, one-way valves 9, 10 and variable diameter joints 11, 12, and then enters the micro-reactor system to start the reaction. The reaction temperature is 80°C, and the reaction residence time is After 32.3 minutes, the crude product was collected at the outlet, and after rotary steaming, the sample was analyzed by HPLC. The conversion rate of rifamycin S was 98.2%, and the yield of benzoxazine rifamycin was 78.1%.

Embodiment 2

[0027] Use N,N-dimethylformamide as solvent to prepare 0.386M rifamycin S solution 1 and 1.362M dimethylol-tert-butylamine solution 2, and both materials pass through the metering pump 3 and metered at a flow rate of 0.3mL / min. Pump 4, through two-way ball valves 7,8, one-way valves 9,10 and reducing joints 11,12, is transported to the micro-mixer 16 and then enters the micro-reactor system to start the reaction. The reaction temperature is 70°C, and the reaction residence time is After 32.3 minutes, the crude product was collected at the outlet, and after rotary steaming, the sample was analyzed by HPLC. The conversion rate of rifamycin S was 98.9%, and the yield of benzoxazine rifamycin was 95.9%.

Embodiment 3

[0029] Use N,N-dimethylformamide as solvent to prepare 0.392M rifamycin S solution 1 and 1.362M dimethylol-tert-butylamine solution 2, and both materials pass through metering pump 3 and metered at a flow rate of 0.242mL / min. Pump 4, through two-way ball valves 7,8, one-way valves 9,10 and reducing joints 11,12, is transported to the micro-mixer 16 and then enters the micro-reactor system to start the reaction. The reaction temperature is 70°C, and the reaction residence time is After 40 minutes, the crude product was collected at the outlet, and after rotary steaming, the sample was analyzed by HPLC. The conversion rate of rifamycin S was 98.3%, and the yield of benzoxazine rifamycin was 93.6%.

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Abstract

The invention discloses a method for continuously preparing benzoxazine rifamycin. The method comprises the following steps: 1) dissolving rifamycin S into an organic solvent, performing filtering soas to obtain a homogeneous solution of rifamycin S; 2) dissolving dihydroxymethyl tert-butylamine into an organic solvent, and performing sufficient mixing so as to obtain a homogeneous solution of dihydroxymethyl tert-butylamine; 3) continuously pumping the two homogeneous solutions obtained in steps 1) and 2) into a micro-reactor for mixing, enabling the mixed materials to react in a second reactor of the micro-reactor so as to obtain a product benzoxazine rifamycin; and 4) performing aftertreatment on samples, and performing external standard quantitative analysis on the samples by using ahigh performance liquid chromatography method, so as to obtain the content of benzoxazine rifamycin in the samples. By adopting the method disclosed by the invention, the characteristics of efficientmass transfer and heat transfer of the micro-reactor are utilized, and with optimized reaction parameters, the reaction time can be shortened to 30 minutes, and the product yield is 95% or greater.

Description

technical field [0001] The invention relates to a method for continuously preparing benzoxazine rifamycin, in particular to a method for continuously preparing benzoxazine rifamycin by using micro-reaction technology, and belongs to the field of organic synthesis. Background technique [0002] Benzoxazine rifamycin is used as an intermediate for the synthesis of rifampicin, and rifampin (Rifampin) is a broad-spectrum antibiotic, except that it has high activity against Mycobacterium tuberculosis, it is effective against Bacillus leprae, non-enterococcus Streptococcus, pneumococcus and other Gram-negative bacteria, especially the drug-resistant aureus rifamycin antibiotic Staphylococcus aureus are very strong. It is also effective against certain Gram-negative bacteria, and it is often used in combination with other anti-tuberculosis drugs to treat various types of tuberculosis and severe infections of drug-resistant Staphylococcus aureus, and is also used to treat leprosy. ...

Claims

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Application Information

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IPC IPC(8): C07D498/18
CPCC07D498/18
Inventor 陈光文温正慧韩梅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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