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Intermediate for preparing linezolid

A technology of linezolid and furfuralimine, which is applied in the field of drug synthesis and can solve problems such as environmental damage, high toxicity, and loss

Active Publication Date: 2012-01-04
ZHEJIANG YATAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because these aldehydes are highly toxic, if they exist in products or are lost in waste water, they will cause great harm to the human body and the environment

Method used

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  • Intermediate for preparing linezolid
  • Intermediate for preparing linezolid
  • Intermediate for preparing linezolid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment 1: the preparation of furfural imine

[0088]

[0089] Add 20 g of furfural and 32 ml of ammonia water into the reaction flask, stir, and react overnight at room temperature. Suction filter the reaction product, wash the filter cake with a small amount of water, and dry to obtain 19.2 g of furfural imine.

Embodiment 2

[0090] Embodiment 2: Preparation of (S)-1-chloro-3-[(furan-2-methylene)amino]propan-2-ol (structural formula II)

[0091]

[0092] In the reaction flask, 19.2 g of furfural imine prepared in Example 1, 120 ml of methyl tert-butyl ether, and 16 ml of S-epichlorohydrin were added. Stir for 30 minutes, slowly heat to reflux, react for 6 hours, cool to room temperature, concentrate to dryness under reduced pressure at 40°C, add 30ml of methyl tert-butyl ether to dissolve, crystallize in the refrigerator, filter with suction, filter cake with cold methyl tert-butyl ether After washing with butyl ether and vacuum drying to constant weight, 29.2 g of the product was obtained with a yield of 78%.

[0093] product of 1 H-NMR (400MHz, CDCl 3 ): 2.92 (bs, 1H, OH), 3.60-3.70 (m, 2H, NCH2), 3.70-3.80 (m, 2H, ClCH2), 4.16-4.19 (m, 1H, OCH), 6.48-6.50 (te, 1H, Fu-4-H), 6.79 (d, 1H, Fu-3-H), 7.53 (d, 1H, Fu-5-H), 8.14 (S, 1H, N=CH), as (S) -1-Chloro-3-[(furan-2-methylene)amino]propan-2...

Embodiment 3

[0094] Embodiment 3: Preparation of (S)-1-chloro-3-[(furan-2-methylene)amino]propan-2-ol (structural formula II)

[0095]

[0096]In the 500ml reaction bottle, add 48.0g furfural, 1160ml 95% ethanol and 45.7g ammoniacal liquor (28.8%), stir 10 minutes, add S-epichlorohydrin 46.3g, reaction exotherm, stir 1 hour, temperature rises automatically About 40°C. Heated, kept at 35-40°C, reacted for 6 hours, stirred at room temperature for 13.5 hours, concentrated to about 50ml, cooled to crystallize, filtered out the solid, and dried to obtain 47.8g of the product, with a yield of 48%.

[0097] product of 1 H-NMR (400MHz, CDCl 3 ) 2.92 (bs, 1H, OH), 3.60-3.70 (m, 2H, NCH2), 3.70-3.80 (m, 2H, ClCH2), 4.16-4.19 (m, 1H, OCH), 6.48-6.50 (te, 1H , Fu-4-H), 6.79 (d, 1H, Fu-3-H), 7.53 (d, 1H, Fu-5-H), 8.14 (S, 1H, N=CH), as (S)- 1-Chloro-3-[(furan-2-methylene)amino]propan-2-ol (Formula II).

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Abstract

The invention discloses an intermediate for preparing linezolid, which is a compound shown in a structural formula I. The invention further discloses a method for preparing the compound shown in the structural formula I. The method comprises the steps of reacting S)-1-chlorine-3-[(furan-2-methylene)amino]propyl-2-alcohol and N-carboxybenzyl-3-fluorin-4-morpholine phenylamine and generating the compound shown in the structural formula I. According to the method disclosed by the invention, raw and auxiliary materials are low in cost and are easy to obtain; furthermore, the process route is short; the cost is low; the reaction condition is moderate and safe; the device does not have specific requirements; and the method is applied to industrial production.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to an intermediate used for preparing antibacterial drug linezolid. Background technique [0002] Bacterial drug resistance is one of the most serious problems facing global clinical and public health. Due to its unique chemical structure and mechanism of action, Linezolid is effective against drug-resistant bacteria, especially vancomycin-resistant bacteria. Better killing effect. Linezolid (represented by structural formula VII), chemical name (S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl ]Methyl]acetamide is the first oxazolidinone antibacterial drug launched by Pfizer in 2000, mainly used to treat drug-resistant bacterial infections and surgical infections. [0003] [0004] Structural formula VII. [0005] For the synthesis of linezolid, the processes reported in the literature can be roughly divided into two categories, one is the sodium azide process, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D263/20
Inventor 金春华吕旭幸胡国庆王丽云朱勤丰张礼芳雷灵芝
Owner ZHEJIANG YATAI PHARMA
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