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Evaporation crystallization process for linezolid with crystal form I

A technology of linezolid and evaporation crystallization, which is applied in the field of compound synthesis technology, can solve problems such as difficulty in realizing industrial production, low yield, and difficult solvent recovery, and achieve low solvent usage, high yield, and fast evaporation speed Effect

Active Publication Date: 2011-05-25
ZHEJIANG LEPU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process of crystal form Ⅰ reported in the literature (J Med. Chem. 39(3) 673-679, 1996) uses column separation, which is difficult to achieve industrial production. A mixed solvent of ethyl acetate and n-hexane is used, and solvent recovery is difficult. low rate

Method used

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  • Evaporation crystallization process for linezolid with crystal form I
  • Evaporation crystallization process for linezolid with crystal form I

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 100 g of crude linezolid to a four-neck flask, add 300 g of n-propanol, stir and heat to 90°C for complete dissolution, evaporate 180 g of n-propanol under reduced pressure at 80°C, crystallize by evaporation, and precipitate crystals. Lower the temperature by 10°C, add the evaporated 180g of n-propanol back into the four-neck flask, cool to 20°C, filter, and wash the filter cake with n-heptane with a mass ratio of 90g, at 40°C, -0.09Mpa Vacuum drying gave the crystalline form I linezolid with a yield of about 90.0%. The X-ray powder diffraction (XRPD) pattern of crystalline form I linezolid is shown in figure 1 .

Embodiment 2

[0019] Add 100 g of crude linezolid and 500 g of n-butanol into a four-neck flask, stir and heat to 90°C for complete dissolution, evaporate 350 g of n-butanol under reduced pressure at 95°C, crystallize by evaporation, and precipitate crystals. Cool down to 20°C, add the evaporated 350g of n-butanol back into the four-neck flask, cool to 30°C, filter, and wash the filter cake with n-heptane with a mass ratio of 170g, at 40°C, -0.09Mpa Vacuum drying gave the crystalline form I linezolid with a yield of about 85.5%.

Embodiment 3

[0021] Add 100 g of linezolid crude product and 400 g of isobutanol into a four-necked flask, stir and heat to 90°C for complete dissolution, distill 280 g of isobutanol at 100°C under reduced pressure, crystallize by evaporation, and precipitate crystals. Lower the temperature by 15°C, add the evaporated 280g of isobutanol back into the four-neck flask, cool to 30°C, filter, and wash the filter cake with n-heptane with a mass ratio of 90g, at 50°C, -0.08Mpa Vacuum drying gave the crystalline form I linezolid with a yield of about 87.0%.

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Abstract

The invention discloses an evaporation crystallization process for linezolid with crystal form I. The method comprises the steps of: dissolving 1 weight part of linezolid in 3 to 5 weight parts of alcohol solvents, evaporating 60 to 70 weight percent of alcohol solvents at the temperature of between 70 and 100 DEG C, inducing crystal nuclei of the linezolid with crystal form I in a boiling state,reducing the temperature by 10 to 20 DEG C, adding the evaporated alcohol solvents again, precipitating crystals, filtering, washing a filter cake by using n-heptane, and performing vacuum-drying at the temperature of between 40 and 50 DEG C and under the pressure of -0.08 to -0.09 MPa to obtain the linezolid with crystal form I. In the evaporation process, the using amount of the solvents is small, the evaporation speed is high, evaporated liquor does not contain crystals, and the evaporated liquor can be directly recycled; and the linezolid is not decomposed and deteriorated, yield is high and the quality is good.

Description

technical field [0001] The present invention relates to a compound synthesis process, in particular to an evaporation crystallization process of crystal form I linezolid. Background technique [0002] Linezolid, chemical name: [(S)-N-[[3-(3-fluoro-4morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide], It is an antibacterial drug used for skin infections caused by various bacteria. Molecular formula is C 16 h 20 FN 3 o 4 , has the following structure (1): [0003] [0004] (1) [0005] U.S. Patent No.5688792, European Patent No.717738, Israeli Patent No.110802, Canadian Patent No.2168560, International Patent WO95 / 07171 and Chinese Patents CN 101128442, CN101220001, CN101774978, document J. Med. Chem. 39(3) 673-679, 1996; Tetrahedron Lett., 40(26)4855,1999; Chinese Journal of Pharmaceutical Industry, 2010(41) 1, 61-62, disclosed linezolid and its preparation method. [0006] Linezolid has multiple crystal forms, and it is generally believed that there are thre...

Claims

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Application Information

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IPC IPC(8): C07D263/20
Inventor 管宜溪蒋成君孔佳郎姚晨
Owner ZHEJIANG LEPU PHARMA CO LTD
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