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Preparation method of crystal form I linezolid

A linezolid, type I technology, applied in the field of organic compound synthesis technology, can solve the problems of large environmental pollution, recrystallization, large amount of solvent, etc., and achieves the effects of less environmental pollution, mild conditions, and small amount of solvent

Inactive Publication Date: 2013-01-02
TIANJIN WEIJIE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1. The former method uses column chromatography for purification, and the amount of solvent is large, which is not suitable for industrial production
In addition, recrystallization with a mixed solvent requires the use of multiple solvents, so the pollution to the environment is large and the cost is high
[0007] 2. The latter method needs to evaporate a certain proportion of solvent and cool down to a certain temperature, so the operation is more complicated and cumbersome, and it is not easy to control accurately, and it is difficult to realize in industry
In addition, it is necessary to use the existing crystalline form I linezolid to induce the crystal nucleus, and the process is complicated

Method used

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  • Preparation method of crystal form I linezolid
  • Preparation method of crystal form I linezolid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 6.5g of linezolid crude product into a 250mL four-necked bottle, add 150mL of isobutyl acetate, stir and heat to 120-130°C, after the crude linezolid is completely dissolved, cool to room temperature (20-25°C) under slow stirring , to precipitate crystals, filter, wash the filter cake with 20 mL of isobutyl acetate, and dry at 40° C. to obtain 5.6 g of crystalline form I linezolid, with a yield of 86.2%. Its X-ray powder diffraction (PXRD) pattern is shown in figure 1 . Its 2θ characteristic peaks are 7.3, 9.2, 13.2, 14.1, 14.6, 16.6, 17.8, 19.5, 19.7, 20.8, 22.0, 25.3, 29.3, 29.6±0.2, and it is the Form I crystal form of linezolid.

Embodiment 2

[0019] Add 5g of linezolid crude product into a 250mL four-neck flask, add 120mL of tert-butyl acetate, stir and heat to 100-110°C, after the crude linezolid is completely dissolved, cool to room temperature (20-25°C) under slow stirring, The precipitated crystals were filtered, the filter cake was washed with 20 mL of tert-butyl acetate, and dried at 40° C. to obtain 4.2 g of crystalline form I linezolid with a yield of 85%.

Embodiment 3

[0021] Add 5g of linezolid crude product into a 250mL four-neck flask, add 160mL of isopropyl acetate, stir and heat to 90-100°C, after the crude linezolid is completely dissolved, cool to room temperature (20-25°C) under slow stirring, The precipitated crystals were filtered, the filter cake was washed with 30 mL of isopropyl acetate, and dried at 40° C. to obtain 3.8 g of crystalline form I linezolid with a yield of 76%.

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Abstract

The invention relates to a preparation method of crystal form I linezolid. The method comprises the steps of: adding a linezolid crude product, non-crystal form I linezolid or mixed linezolid crystal into an ester or toluene solvent, wherein the ester solvent is any one selected from ethyl acetate, acetic acid isobutyl ester, tert-butyl acetate, acetic acid isopropyl ester, isopropyl formate, or ethyl formate, and the amount ratio of the ester or toluene solvent to the linezolid crude product, the non-crystal form I linezolid or the mixed linezolid crystal is (5-40mL): 1g; heating and dissolving the linezolid crude product, the non-crystal form I linezolid or the mixed linezolid crystal into the solvent, and cooling to separate out crystal; filtering the mixed liquid; and finally, washing a filter cake by an organic solvent and drying to obtain the crystal form I linezolid. The preparation method of the crystal form I linezolid is less in solvent amount, does not need crystal nucleus induction, only needs dissolving by heating, cooling and filtering, and is simple and convenient to operate and mild in conditions, thus the preparation method is suitable for industrial production; meanwhile, the method is high in yield.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis technology, and in particular relates to a method for preparing linezolid in crystal form I. Background technique [0002] Linezolid (linezolid) is the first clinically used antibacterial drug made by artificial synthesis, mainly used to treat skin infections caused by various bacteria. Its chemical name is [(S)-N-[[3-(3-fluoro-4morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide], and its molecular formula is C 16 h 20 FN 3 o 4 , with the following structure: [0003] [0004] There are many crystal forms of linezolid, and the document J. Med. Chem. 39 (3) 673-679, 1996 discloses a preparation method of linezolid in crystal form I. In the method, the crude product of linezolid is firstly purified by column chromatography, and then recrystallized with ethyl acetate and n-hexane to obtain linezolid in crystal form I, with a yield of 68.8%. Chinese Patent Application...

Claims

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Application Information

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IPC IPC(8): C07D263/20
Inventor 宋洪海于瑞林王良骍马春磊
Owner TIANJIN WEIJIE TECH
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