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Synthesis of linezolid

A technology of linezolid and its synthesis method, applied in organic chemistry, antibacterial drugs, etc., can solve problems such as danger, long reaction route, unfavorable safety production, etc., and achieve the effect of mild reaction conditions and simple steps

Inactive Publication Date: 2008-07-16
ZHEJIANG BOTAI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above methods all have the use of dangerous raw materials tert-butyl lithium and sodium azide, which is not conducive to safe production, and the reaction route is relatively long

Method used

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  • Synthesis of linezolid
  • Synthesis of linezolid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Dissolve 34.6mmol (6.8g) 3-fluoro-4-morpholinoaniline and 38.1mmol (3.85g) N-2(R)-oxirane amide in 50ml isopropanol and react at 80℃ for 20 hours After the solvent was distilled off under reduced pressure, the residue was dissolved with a small amount of dichloromethane and separated by silica gel column chromatography to obtain N-{2(R)-2-[(3-fluoro-4morpholin-4-ylphenyl) )Amino]-2-hydroxyethyl}acetamide 5.98g, the yield is 58.2%.

[0029] Dissolve 20.1mmol (5.98g) N-{2(R)-2-[(3-fluoro-4morpholin-4-ylphenyl)amino]-2-hydroxyethyl}acetamide in 30ml dichloromethane After adding 4ml of pyridine, cool to 0℃ with an ice-water mixture, dissolve 7.4mmol (2.2g) triphosgene solid in 20ml of dichloromethane, slowly add dropwise to the above solution, after the addition, stir at 25℃ for reaction After 2 hours, add triethylamine to adjust the pH to weakly alkaline, extract with dichloromethane, wash with water, saturated brine, dry with anhydrous magnesium sulfate, filter, and evaporate...

Embodiment 2

[0031] Dissolve 25.5mmol (5g) 3-fluoro-4-morpholinoaniline and 28.2mmol (2.85g) N-2(R)-oxirane amide in 35ml isopropanol and react at 70°C for 18 hours, After the solvent was distilled off under reduced pressure, it was dissolved in a small amount of dichloromethane, and separated by silica gel column chromatography to obtain N-{2(R)-2-[(3-fluoro-4morpholin-4-ylphenyl)amino] -2-hydroxyethyl}acetamide 4.5g, yield 59.5%

[0032] Dissolve 15.2mmol (4.5g) N-{2(R)-2-[(3-fluoro-4morpholin-4-ylphenyl)amino]-2-hydroxyethyl}acetamide with 25ml dichloromethane After adding 3ml pyridine, cool to 0℃ with ice-water mixture, dissolve 5.1mmol (1.5g) triphosgene solid in 15ml dichloromethane, slowly add dropwise to the above solution, after addition, stir at 20℃ for reaction After 2 hours, add triethylamine to adjust the pH to weakly alkaline, extract with dichloromethane, wash with water, saturated brine, dry with anhydrous magnesium sulfate, filter, and evaporate the solvent under reduced press...

Embodiment 3

[0034] Dissolve 34.6mmol (6.8g) 3-fluoro-4-morpholinoaniline and 38.1mmol (3.85g) N-2(R)-oxirane amide in 50ml tetrahydrofuran. The reaction temperature is 60℃ to obtain N-{ 2(R)-2-[(3-Fluoro-4morpholin-4-ylphenyl)amino]-2-hydroxyethyl}acetamide 5.6 g, yield 54.5%. The other steps are the same as in Example 1.

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Abstract

The invention relates to a synthetic method for linezolid, which dissolves a 3-fluoro-4- morpholinyl laniline and an N-2(R)-epoxy acetamide in an organic solvent to react for 10 to 30 hours in a temperature of 20 to 100 DEG C, and acquires an N-{2(R)-2-[(3-fluoro-4 morpholine-4-base phenyl) amino]-2-hydroxy ethyl}; then an acquired compound and a carbonylation agent are dissolved in a halohydrocarbon organic solvent and reacted for 0.5 to 5 hours in a temperature of 0-50 DEG C under the catalysis of a base catalyst, thereby acquiring the linezolid. The method of the invention uses an ordinary reagent and normal plant conditions in industry, the reaction condition is mild and the steps are simple.

Description

Technical field [0001] The invention relates to an organic synthesis method, in particular to a synthesis method of linezolid. Background technique [0002] The chemical name of linezolid is: (S)-N-((3-(3-fluoro4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl) Acetamide [0003] The structural formula I of linezolid is as follows: [0004] [0005] Linezolid (Linezolid) is a fluorine-containing oxazolidone antibacterial drug developed by Pharmacia & Upjohn Company. The drug can treat nosocomial infectious pneumonia, skin and soft tissue infections, community infectious pneumonia and other diseases, and its efficacy has been confirmed by clinical studies. In addition, the clinical efficacy of linezolid is better than or equivalent to conventional antibacterial drugs, and it is resistant to infections caused by methicillin-resistant Staphylococcus (MRSA), glycopeptide-resistant enterococcus, and penicillin-resistant pneumococcus (PRSP). It is also effective, with little toxic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/18A61P31/04
Inventor 王敏童华光
Owner ZHEJIANG BOTAI CHEM
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