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A kind of preparation method of linezolid

A technology of linezolid and phthalimide potassium salt is applied in the field of preparation of linezolid, which can solve the problem that it is difficult to meet the purity requirements of linezolid, the purification operation and the anhydrous requirements are harsh, and the atoms/processes are inconsistent. Economic and other issues, to achieve the effect of efficient preparation, high product yield and fast reaction

Active Publication Date: 2019-06-18
SHANDONG YUXIN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, lithium alkoxides (such as lithium tert-butoxide, lithium tert-amyloxide, etc.) are easy to absorb moisture and are not easy to store, and commercially available lithium alkoxides are difficult to meet the purity requirements for the preparation of linezolid no matter whether they are reagent grade or industrial grade, so they are often The reaction is promoted with freshly prepared lithium alkoxide
Taking the preparation of lithium tert-butoxide as an example, the document OrganicSyntheses, 1988, 6, 259 reported that lithium tert-butoxide was prepared by reacting tert-butanol and n-butyllithium, and directly participated in the esterification reaction after the solvent was evaporated; this method is feasible but the atom / process Uneconomical, demanding purification operations and anhydrous

Method used

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0049] Embodiment 1-1: Synthesis of Compound 3

[0050] Add phthalimide potassium salt (55.6g, 0.3mol), (S)-4-chloro-1,3-butanediol (compound 1, 37.4g, 0.3mol) and 300mLDMF into the reaction flask, heat After reacting at 80°C for 3 hours, the reaction solution was poured into 400 mL of water, stirred for 10 minutes, filtered with suction, and dried under reduced pressure to obtain 65.4 g of white solid (Compound 2), with a yield of 92.3%.

Embodiment 1-2

[0051] Embodiment 1-2: the synthesis of compound 3

[0052] Add phthalimide potassium salt (66.7g, 0.36mol), (S)-4-chloro-3-hydroxybutyronitrile (compound 1, 37.4g, 0.3mol) and 300mL DMF into the reaction flask, heat to 70 After reacting at ℃ for 5 h, the reaction solution was poured into 400 mL of water, stirred for 10 min, filtered with suction, and dried under reduced pressure to obtain 68.6 g of white solid (Compound 2), with a yield of 96.8%.

Embodiment 2-1

[0053] Embodiment 2-1: Synthesis of compound 4

[0054] in N 2 Under the condition of protection, add 47.3g of compound 2 (0.2mol) into the reaction flask with magnets, add 2000mL of ethyl acetate, put the reaction flask into an ice-water bath to cool down to 0°C, and then add PhICl 2 (218.3g, 0.8mol) and NaN 3 (104.0g, 1.6mol), the reaction was stirred at 0°C for 4h, then heated to 80°C and stirred for 8h. The reaction system was lowered to room temperature, 2000 mL of ethyl acetate was added, and it was transferred to a separatory funnel, and saturated Na 2 S 2 0 3 solution (1500mL), the separated aqueous phase was extracted with ethyl acetate (2×500mL), the combined organic phases were washed with saturated brine (500mL), anhydrous Na 2 S0 4 After drying, the organic solvent was removed by rotary evaporation to obtain 46.1 g of compound 4 with a HPLC purity of 99.2% and a yield of 93.3%.

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Abstract

The invention discloses a preparation method of linezolid. (S)-4-chloro-1,3-butanediol (compound 1) is taken as a raw material, and linezolid is obtained after potassium phthalimide substitution, Curtius rearrangement ring closure, Ullmann coupling, hydrazinolysis and amidation; a synthesis process causes small pollution and is easy to treat, the yield and purity in each step are high, and the method is environment-friendly, low in production cost and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a preparation method of linezolid. Background technique [0002] Linezolid (Linezolid, 1), also known as linezolid, linezolid, ranezolid, chemical name: (S)-N-[[3-(3-fluoro-4-morpholinophenyl) -2-oxo-5-oxazolidinyl]methyl]acetamide, CASNo: 165800-03-3, is the first new type of oxazolidinone (oxazolidnone) antibacterial drug used in clinical practice. It is a new type of oxazolidinone fully synthetic antibacterial drug developed and produced by Pharmacia & Upiohn Company of the United States (which has been acquired by Pfizer). The U.S. FDA approved the drug for marketing on April 18, 2000. The trade name is Zyvox. This product is the first drug approved in the United States for the treatment of methicillin-resistant Staphylococcus aureus infection in the past 40 years. It was listed in my country in September 2007 and belongs to the Class B drug of medica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/20
CPCC07D263/20
Inventor 于德峰赵长生相光西
Owner SHANDONG YUXIN PHARMA CO LTD
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