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Synthesis process of linezolid intermediate

A synthesis process and linezolid technology, applied in the field of pharmaceutical chemistry, can solve the problems of high risk of acetone use, numerous post-processing steps, environmental pollution, etc., and achieve low price, reduce the possibility of residual solvents, and reduce pollution. Effect

Inactive Publication Date: 2015-04-22
甘肃普安制药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the use of acetone is more dangerous, and there are many post-processing steps, which will cause a decrease in yield, an increase in cost, and a corresponding increase in environmental pollution during production.

Method used

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  • Synthesis process of linezolid intermediate
  • Synthesis process of linezolid intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 10 g of 3,4-difluoronitrobenzene, 8.70 g of morpholine, and 6.66 g of sodium carbonate to 40 g of methyl ethyl ketone in sequence, raise the temperature under stirring, reflux at 75°C for 5 hours, filter, and concentrate to obtain 13.91 g of compound (2 ), yield: 97.83%;

[0032] Add 13.91g of compound (2) into the reaction flask, add 210g of butanone, stir and add 0.1g of palladium carbon catalyst, nitrogen replacement system 4 times, hydrogen replacement system 4 times, and react at 35°C for 16 hours to obtain compound (3) The reaction solution;

[0033] The reaction solution of compound (3) was filtered, and 10.33g NaHCO was added 3 , filter off the hydrogenation reaction catalyst, under the protection of nitrogen, lower the temperature to 7°C, add dropwise 13.64g of benzyl chloroformate, keep the system temperature below 10°C, after the dropwise addition, keep the temperature at 25°C for 1h to obtain 19.14g of compound (4), and collect Rate: 94.22%;

[0034] ...

Embodiment 2

[0036] Add 10 g of 3,4-difluoronitrobenzene, 8.6 g of morpholine, and 6.8 g of sodium carbonate to 41 g of methyl ethyl ketone in sequence, raise the temperature under stirring, reflux at 76°C for 5.5 hours, filter, and concentrate to obtain 13.71 g of the compound (2 ), yield: 96.43%;

[0037] Add 13.71g of compound (2) into the reaction flask, add 220g of butanone, stir and add 0.1g of palladium carbon catalyst, nitrogen replacement system 4 times, hydrogen replacement system 4 times, and react at 35°C for 16 hours to obtain compound (3) The reaction solution;

[0038] Filter the reaction solution of compound (3), add 10.18gNaHCO 3 , filter off the hydrogenation reaction catalyst, under the protection of nitrogen, lower the temperature to 7°C, add 13.44g of benzyl chloroformate dropwise, keep the system temperature below 10°C, after the dropwise addition, keep the temperature at 25°C for 1h to obtain 19.01g of compound (4), and collect Rate: 94.73%;

[0039] Calculate the...

Embodiment 3

[0041] Add 10 g of 3,4-difluoronitrobenzene, 8.7 g of morpholine, and 6.8 g of sodium carbonate to 41 g of methyl ethyl ketone in sequence, heat up while stirring, reflux at 76°C for 6 hours, filter, and concentrate to obtain 13.66 g of the compound (2 ), yield: 96.07%;

[0042] Add 13.66g of compound (2) into the reaction flask, add 240g of butanone, stir and add 0.1g of palladium carbon catalyst, nitrogen replacement system 4 times, hydrogen replacement system 4 times, and react at 35°C for 16 hours to obtain compound (3) The reaction solution;

[0043] Filter the reaction solution of compound (3), add 10.5g NaHCO 3 , filter off the hydrogenation reaction catalyst, under the protection of nitrogen, lower the temperature to 7°C, add 13.40 g of benzyl chloroformate dropwise, keep the system temperature below 10°C, and react at a constant temperature of 25°C for 1 hour after the dropwise addition to obtain 19.00 g of compound (4). Rate: 95.24%;

[0044] Calculate the yield: ...

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Abstract

The invention discloses a synthesis process of a linezolid intermediate. The method comprises the following steps: with 3,4-difluoronitrobenzene (1) as a raw material, preparing 3-fluorine-4-morpholinyl nitrobenzene (2) through nucleophilic substitution with morpholine; carrying out nitro reduction reaction on the 3-fluorine-4-morpholinyl nitrobenzene (2), and adopting Pd / C reduction, so as to obtain 3-fluorine-4-morpholinoaniline (3); and processing the 3-fluorine-4-morpholinoaniline (3) by virtue of a chloro-carbonic ester method, and carrying out aminolysis reaction on benzyl chloroformate and 3-fluorine-4-morpholinoaniline, so as to obtain a product N-(3-fluorine-4-morpholine phenyl) benzyl carbamate (4). The process disclosed by the invention is simple in reagent, low in price, few in synthesis steps, and relatively mature in synthesis route; the time is shortened; the cost is reduced; unnecessary impurities and by-products, which can be introduced in the experiment treatment process are reduced; the pollution to environment is reduced; and industrialized production is facilitated.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemistry, in particular to a synthesis process of a linezolid intermediate. Background technique [0002] The main components of linezolid intermediates and their chemical names are: benzyl N-(3-fluoro-4-morpholinephenyl)carbamate (4) [0003] CAS: 168828-81-7 [0004] Molecular formula: C 18 H19F 2 o 3 [0005] Molecular weight: 330.35 [0006] The compound is an intermediate in a method for synthesizing linezolid, which is a novel oxazolidinone fully synthetic antibacterial drug developed and produced by Pfizer of the United States. The U.S. FDA approved the drug on April 18, 2000. The trade name is Zyvox, which is used to treat infections caused by Gram-positive cocci (including concurrent bacteremia), and nosocomial infections caused by Staphylococcus aureus or Streptococcus pneumoniae. Acquired pneumonia; complicated and uncomplicated skin or skin and soft tissue infections, co...

Claims

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Application Information

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IPC IPC(8): C07D295/135
CPCC07D295/135
Inventor 金鑫祝可锦
Owner 甘肃普安制药股份有限公司
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