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Method for synthesizing florfenicol midbody RT0131

A technology of RT0131 and florfenicol, which is applied in the field of synthesizing florfenicol intermediates, can solve the problems of high requirements on container and reaction conditions, low yield of finished products, inconvenient operation, etc., and achieve reduced production costs, high conversion efficiency, The effect of less by-products

Inactive Publication Date: 2012-06-13
JIANGXI RISHANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the main problem of synthesizing Florfenicol intermediates is that there are many by-products in the synthesis of Florfenicol intermediates, and they are not easy to separate, and the yield of finished products is low; inconvenient

Method used

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  • Method for synthesizing florfenicol midbody RT0131
  • Method for synthesizing florfenicol midbody RT0131
  • Method for synthesizing florfenicol midbody RT0131

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Example 1: RT0130-A generates RT0130-SM through alkaline hydrolysis deamidation

[0088] Add 50.0 g (0.14 mol) of solid RT0130-A into 373 ml of sodium hydroxide solution (1.5 mol / L, 0.56 mol), stir rapidly at 60°C for 2.5 hours, cool to room temperature, add 500 ml of methyl tert-butyl ether for extraction , the organic phase was separated, concentrated, and dried in vacuo to obtain RT0130-SM as a white solid.

[0089] Feeding ratio (molar ratio):

[0090] RT0130-A:NaOH=1:4

[0091] Solvent: ethanol

[0092] The chemical reaction formula is as follows:

[0093]

Embodiment 2

[0094] Example 2: RT0130-SM reacts and condenses with phenylacetonitrile to generate RT0130

[0095]Dissolve 24.5 grams (0.10 moles) of RT0130-SM and 20.7 grams (0.15 moles) of anhydrous potassium carbonate in 46 milliliters of glycerol, stir and heat to 115°C, and dissolve 19.0 grams of benzonitrile (PhCN) within half an hour Add the above white suspension solution dropwise, keep warm and stir rapidly for 18 hours, TCL detects that the reaction is complete, cool to room temperature, add 400 ml of ice water to dilute and stir evenly, keep warm at 4-10°C for 1 hour, filter, wash with ice water, Drying in vacuo yielded 31.5 g (0.095 mol) of RT0130 as a white solid.

[0096] Feeding ratio (molar ratio)

[0097] RT0130-SM: benzonitrile: potassium carbonate = 1.00: 1.85: 1.50

[0098] Protic Solvent: Glycerol

[0099] The chemical reaction formula is as follows:

[0100]

Embodiment 3

[0101] Example 3: RT0130 was fluorinated by XtalFluor-E to generate RT0131

[0102] 31.5 g (0.095 mol) of solid RT0130 were dissolved in 315 mL of dry dioxane. Slowly add potassium carbonate (0.28 mole) and solid XtalFluor-E (0.28 mole) reagent under nitrogen protection, after stirring well, slowly rise to room temperature and stir reaction for 24 hours, TLC (Thin Layer Chromatography, thin plate chromatography) detects reaction Finish. The reaction liquid was slowly poured into ice-cold potassium bicarbonate aqueous solution (0.1 mol / L), the organic phase was separated, decolorized with 5% activated carbon, dried, and concentrated to obtain 28.5 g (0.090 mol) of RT0131 as a light yellow-brown solid.

[0103] Feeding ratio (molar ratio)

[0104] RT0130:K 2 CO 3 : XtalFluor-E reagent = 1.00: 2.95: 2.95

[0105] Solvent: Dioxane

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Abstract

The invention provides a method for synthesizing a florfenicol midbody RT0131, which comprises the following steps of: dissolving RT0130 into an aprotic polar solvent and leading RT0130 to generate fluorination reaction under XtalFluor-E and base catalysis so as to generate the florfenicol midbody RT0131. On the other hand, the invention provides a method for generating thiamphenicol into the florfenicol midbody RT0131 through hydrolysis, condensation and fluorination reaction. The method has the advantages of convenience in operation, less by-products, easiness for purification of products and good environmentally-friendly effect.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for synthesizing a florfenicol intermediate. Background technique [0002] Since 1957, the research on fluorine-containing drugs has made continuous progress. At present, 150 kinds of fluorine-containing drugs have been marketed in the world, accounting for 20% of the total number of drugs, and fluorine-containing pesticides are even as high as 30%. Researchers have increasingly realized that the introduction of fluorine atoms or fluorine-containing groups in organic molecules may bring about subtle changes in biological activity of organic molecules. Since the 1970s, my country has successively carried out organic In the past 20 years, my country has made remarkable achievements in the research and development of fluorine-containing intermediates and fine chemicals, and has entered a period of vigorous development. [0003] Florfenicol (Florfenicol), also known as flor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/10
Inventor 周鹏周显志彭陟辉孙国斌边峰
Owner JIANGXI RISHANG CHEM
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