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Reagent and method for splitting ofloxacin racemate by using ionic liquid and l-dibenzoyl tartaric acid

A ‐dibenzoyl tartaric acid, ionic liquid technology, applied in the field of chemical separation of chiral medicines, can solve the problems of difficulty in the separation of ofloxacin racemates and unfavorable industrial applications, and reduce the reagents required for separation , the effect of improving efficiency and simple operation process

Active Publication Date: 2015-10-07
CHINA CONSTR IND & ENERGY ENG GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The separation factors of various resolution methods currently used are all within 1.4, and the resolution of ofloxacin racemate is difficult, which is not conducive to industrial application

Method used

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  • Reagent and method for splitting ofloxacin racemate by using ionic liquid and l-dibenzoyl tartaric acid
  • Reagent and method for splitting ofloxacin racemate by using ionic liquid and l-dibenzoyl tartaric acid
  • Reagent and method for splitting ofloxacin racemate by using ionic liquid and l-dibenzoyl tartaric acid

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Experimental program
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Effect test

Embodiment 1

[0019] Ofloxacin racemate and 1-ethyl-3-methylimidazole L-tartrate were dissolved in deionized water to form 1-ethyl-3-methylimidazole L-tartrate with a concentration of 0.05mol / L , the concentration of ofloxacin racemate is an aqueous phase of 1000ppm, and simultaneously L-dibenzoyltartaric acid is dissolved in n-decyl alcohol to form an organic phase containing L-dibenzoyltartaric acid concentration of 0.15mol / L. Mix the organic phase and the aqueous phase with a volume ratio of 1:1 and put them in a shaker, shake for 2 hours, let stand, take the aqueous phase clear liquid to detect the concentration of L-ofloxacin and D-ofloxacin respectively, and the separation factor Reached 3.6.

Embodiment 2

[0021] Ofloxacin racemate and 1-ethyl-3-methylimidazole L-tartrate were dissolved in deionized water to form 1-ethyl-3-methylimidazole L-tartrate with a concentration of 0.05mol / L , the concentration of ofloxacin racemate is an aqueous phase of 1000ppm, and simultaneously L-dibenzoyltartaric acid is dissolved in n-decyl alcohol to form an organic phase containing L-dibenzoyltartaric acid concentration of 0.5mol / L. Mix the organic phase and the aqueous phase with a volume ratio of 1:1 and put them in a shaker, shake for 2 hours, let stand, take the aqueous phase clear liquid to detect the concentration of L-ofloxacin and D-ofloxacin respectively, and the separation factor reached 1.73.

Embodiment 3

[0023] Ofloxacin racemate and 1-ethyl-3-methylimidazole L-tartrate were dissolved in deionized water to form 1-ethyl-3-methylimidazole L-tartrate with a concentration of 0.05mol / L , the concentration of ofloxacin racemate is an aqueous phase of 1000ppm, and simultaneously L-dibenzoyltartaric acid is dissolved in n-decyl alcohol to form an organic phase containing L-dibenzoyltartaric acid concentration of 0.05mol / L. Mix the organic phase and the aqueous phase with a volume ratio of 1:1 and put them in a shaker, shake for 2 hours, let stand, take the aqueous phase clear liquid to detect the concentration of L-ofloxacin and D-ofloxacin respectively, and the separation factor reached 1.97.

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Abstract

The invention discloses reagents and a method for separation of ofloxacin racemic mixture by utilization of ionic liquid and L-dibenzoyltartaric acid together. Ofloxacin racemic mixture and alkyl imidazole L-tartrate ionic liquid are dissolved in deionized water and a water phase is formed. At the same time, L-dibenzoyltartaric acid is dissolved in n-decyl alcohol and an organic phase is formed. The organic phase and the water phase are mixed and placed in a vibrator for vibration, and then the mixture is permitted to stand. The concentrations of L-ofloxacin and D-ofloxacin in the water-phase clear solution are detected. The concentrations of L-ofloxacin and D-ofloxacin in the organic phase are obtained through a law of conservation of mass respectively. The distribution coefficients of L-ofloxacin and D-ofloxacin are calculated respectively, and therefore the separation factor is calculated, the separation effect is good and the separation is successful. Separation of ofloxacin racemic mixture is achieved by utilization of alkyl imidazole L-tartrate ionic liquid and L-dibenzoyltartaric acid together, the separation efficiency is raised, required reagents for separation are reduced, the operation technology is simple, the selectivity is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the chemical separation of chiral medicines, in particular to a reagent and method for splitting racemates of ofloxacin by using ionic liquid and L-dibenzoyl tartaric acid. Background technique [0002] Ofloxacin racemate is a broad-spectrum antibacterial fluoroquinolone. Ofloxacin racemate is easy to absorb when taken orally, and its mechanism of action is to inhibit bacterial DNA gyrase, and its clinical application has remarkable curative effect. L-ofloxacin is one of the chiral isomers of the racemate of ofloxacin. L-ofloxacin has more advantages than ofloxacin racemate, its antibacterial activity is 2 times of ofloxacin racemate, water solubility is 8 times of ofloxacin racemate, its Less toxic and side effects. [0003] The enantiomeric separation factor is an important factor to investigate the effect of chiral resolution. It is defined as the ratio of the distribution coefficients of two isomers. Generally speaking, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/06C07B57/00
CPCC07D498/06
Inventor 陈冬璇罗能镇张本贺相咸高何潮洪徐义明周俊超岳昌海
Owner CHINA CONSTR IND & ENERGY ENG GRP CO LTD
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