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Preparation method of florfenicol intermediate

A technology of florfenicol and intermediates, applied in the field of preparation of florfenicol intermediates, can solve problems such as unsatisfactory, increased process, increased process investment, etc., to reduce raw material input costs, simple process, avoid The effect of complex processes

Active Publication Date: 2019-10-15
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this process has effectively changed the color and impurity content of Florfenicol, it has correspondingly increased some process investment, the process has increased, and the method of fluorination with Ishikawa reagent has not been changed, which is still unsatisfactory

Method used

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  • Preparation method of florfenicol intermediate
  • Preparation method of florfenicol intermediate
  • Preparation method of florfenicol intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Production of special potassium fluoride: Weigh 58 grams of potassium fluoride and dissolve it in 480 ml of methanol. After heating and refluxing for 1 hour at 65°C, the methanol is recovered under reduced pressure at 30°C. After drying in a vacuum box at ℃ for 7 hours, a fluffy cotton-like special potassium fluoride product is obtained. The product effectively increases the specific surface area of ​​potassium fluoride, thereby greatly increasing the activity of potassium fluoride (other examples Omit this manufacturing method).

[0028] Take 10g of the prepared cyclic compound oxazoline, then take 50.25g of dichloromethane, stir to dissolve the cyclic compound in dichloromethane, and then add 4.57g of thionyl chloride dropwise to the dichloromethane of the cyclic compound In the methane solution, the temperature was kept at 15°C during the period, and the reaction was kept for 90 minutes. Then add 2.06g of special potassium fluoride to it and heat it at 30℃ for one hour...

Embodiment 2

[0030] Take 10g of the prepared cyclic compound oxazoline, then take 50.25g of dichloromethane, stir to dissolve the cyclic compound in dichloromethane, and then add 4.93g of thionyl chloride dropwise to the dichloromethane of the cyclic compound In the methane solution, the temperature was kept at 15°C during the period, and the reaction was kept for 90 minutes. Then special potassium fluoride 2.06 was added to it and the reaction was kept at 30°C for one hour. After the reaction was completed, the dichloromethane was recovered. First, the dichloromethane was recovered under normal pressure, and the temperature was raised to 65°C and then recovered under reduced pressure. The mass yield of oxazoline was 96.2%.

Embodiment 3

[0032] Take 10g of the prepared cyclic compound oxazoline, then take 50.25g of dichloromethane, stir to dissolve the cyclic compound in dichloromethane, and then add 5.28g of thionyl chloride dropwise to the dichloromethane of the cyclic compound In the methane solution, the temperature was kept at 15°C during the period, and the reaction was kept for 90 minutes. Then add 2.03g of special potassium fluoride to it and heat it at 30℃ for one hour. After the reaction is completed, the dichloromethane is recovered. First, the dichloromethane is recovered under normal pressure, and the temperature is raised to 65℃ and then recovered under reduced pressure to obtain fluoride. The mass yield of oxazoline was 96.1%.

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Abstract

The invention discloses a preparation method of a florfenicol intermediate. A cyclic compound oxazoline used as a starting material is chlorinated by thionyl chloride, and then is fluorinated by potassium fluoride to successfully introduce a fluorine atom, so a novel process synthesis method for preparing the florfenicol intermediate fluorinated oxazoline is developed. The preparation method has the advantages of simple process, low raw material investment, high product yield and strong market competitiveness.

Description

Technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, and particularly relates to a preparation method of florfenicol intermediates. Background technique [0002] Florfenicol is a new generation of chloramphenicol broad-spectrum antibiotics. It can be used to treat Gram-positive, Gram-negative and rickettsia-induced infections. It has a wide range of uses in clinical medicine and agriculture. There are many synthetic process routes for florfenicol, and most of the synthesis is from the starting material to the intermediate to the finished florfenicol. [0003] Patent US5382673 introduces a method of using D-threo-p-methylsulfonyl phenylserine ethyl ester by potassium borohydride reduction, dichloroacetonitrile cyclization, reaction to obtain the cyclic compound oxazoline (also known as (4R, 5R)- 2-(1,1-Dichloromethyl)-4-hydroxymethyl-5-(4-methylsulfonylphenyl)-4,5-oxazoline). The cyclic compound oxazoline was fluorinated with Ishikaw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/10
CPCC07D263/10
Inventor 刘畅刘聪赵肖泽刘磊
Owner SHANDONG GUOBANG PHARMA
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