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A kind of preparation method of linezolid

A technology of linezolid and triethylamine, which is applied in the field of preparation of linezolid, can solve the problems of low total yield, high cost, difficulty in industrial production of linezolid, etc., achieve mild and easy-to-control reaction conditions, simplify operation, avoid Effect of column separation process

Active Publication Date: 2016-03-02
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0029] To sum up, in the synthetic route mentioned above, there is a widespread use of explosive sodium azide, or the use of n-butyllithium in an anhydrous and oxygen-free ultra-low temperature environment, or high-pressure catalytic hydrogenation, or the use of violent Toxic phosgene, low total yield, and high cost have brought certain difficulties to the industrial production of linezolid

Method used

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  • A kind of preparation method of linezolid
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  • A kind of preparation method of linezolid

Examples

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Effect test

Embodiment 13

[0054] The preparation of embodiment 13-fluoro-4-morpholine nitrobenzene

[0055] In a 3L three-necked flask, install a mechanical stirrer and a thermometer respectively, add 150g (1.72mol) of morpholine, 175g (1.73mol) of triethylamine and 800mL of ethyl acetate, stir well at room temperature, and slowly add 3,4-difluoro 250g (1.57mol) of nitrobenzene was added dropwise within 40min, and stirred at room temperature for 24h, a large amount of yellow solid was formed. TLC showed that the reaction was complete. The reaction mixture was poured into 2.8L of ethyl acetate, fully stirred to dissolve, the solution was washed with water and saturated brine respectively, separated, dried, filtered, and the filtrate was concentrated and crystallized to obtain 351.3 g of a golden yellow solid. The yield is 99.0%.

Embodiment 23

[0056] The preparation of embodiment 23-fluoro-4-morpholine aniline

[0057] In a 3L three-necked flask, add a mechanical stirrer and a thermometer respectively, add 100g (0.44mol) of 3-fluoro-4-morpholine nitrobenzene, 1L of acetone, 3.0g of 10%Pd / C and 137.5g (2.18mol) of ammonium formate ), fully stirred, heated up to 50°C, stirred and reacted for 8 hours, TLC showed that the reaction had been completed, then added 500 mL of acetone, stirred evenly, aged for 2 hours, filtered, and the filtrate was concentrated to dryness to obtain 96 g of off-white solid, the product was not purified. used directly in the next reaction.

Embodiment 3

[0058] The preparation of embodiment 3N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline

[0059] In a 3L three-necked flask, add 96g of unpurified 3-fluoro-4-morpholine aniline, 1.8L of acetone, 800mL of water and 73.9g (0.88mol) of sodium bicarbonate, stir well, and cool down to 0~5°C in an ice-water bath , and then slowly dropwise added 90.0 g (0.53 mol) of benzyl chloroformate, after the dropwise addition was completed, it was slowly raised to room temperature, and the reaction was stirred overnight. The reaction mixture was poured into ice water to precipitate a solid, which was left to stand for 2 h, filtered, washed with water and ethanol, and dried to obtain 132 g of an off-white solid with a yield of 91.0%.

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Abstract

The invention relates to a linezolid (1) preparation method. The method comprises the following steps: reacting a raw material 3,4-difluoronitrobenzene with morpholine, reducing, reacting with benzyl chloroformate to obtain N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline, carrying out a ring closure reaction of N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline and (S)-N-(2,3-epoxypropyl)phthalimide, ammonolyzing, and acetylating to obtain linezolid (1).

Description

technical field [0001] The invention relates to a new method for preparing oxazolidinone antibacterial agents. In particular the invention relates to a novel process for the preparation of linezolid. Background technique [0002] Linezolid, the English name is Linezolid, the chemical name is (S)-N-{[3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolinyl ]methyl}acetamide. The molecular formula of linezolid is C 16 h 20 FN 3 o 4 , with a molecular weight of 337.35, it is a white solid with a melting point of 181.0-183.0°C, and its structural formula is as follows: [0003] [0004] Linezolid is the first synthetic oxazolidinone antibiotic, which was researched and developed by Pharmacia & Upjhon Company of the United States. It was approved for marketing by the FDA on April 18, 2000, and its trade name is ZYVOX. The drug can treat nosocomial pneumonia, skin and soft tissue infection, community infectious pneumonia and other diseases, and its efficacy has been confi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/20
Inventor 王红波赵荐飞陈见见
Owner LUNAN PHARMA GROUP CORPORATION
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