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Synthesizing method of oxazolidine compound

A technology of oxazolidinone and synthesis method, applied in the field of synthesis of oxazolidinone compounds, can solve problems such as the influence of reaction speed, and achieve the effects of mild conditions, wide application range and high yield

Inactive Publication Date: 2012-05-16
TORAY FIBER RES INST(CHINA) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, because the reaction is a two-phase system, the reaction rate is also affected to a certain extent.

Method used

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  • Synthesizing method of oxazolidine compound
  • Synthesizing method of oxazolidine compound
  • Synthesizing method of oxazolidine compound

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preparation example Construction

[0027] The preparation method of the phenylethylamine derivatives used in the present invention is as follows: react with commercially available p-methoxyphenethylamine or p-hydroxyphenylethylamine and benzaldehyde, and use tert-butoxycarbonyl chloride or It can be obtained after protection of benzyloxycarbonyl chloride.

[0028] The various organic oxidizing agents used in the present invention are all commercially available and used directly without purification.

[0029] The nuclear magnetic resonance instrument model used in the present invention is: Japan Electronics (JOEL) JNM-ECX400P.

Embodiment 1

[0031]

[0032] Under the protection of nitrogen at room temperature, add 240 mg of raw materials, 15 mL of toluene, and 175 mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) to a 100 mL single-necked bottle to prepare a reaction solution, stir and heat to 86 °C , track the reaction with thin layer chromatography (TLC) until most of the raw materials disappear, stop heating and cool to room temperature, the reaction solution is washed with saturated sodium carbonate solution, extracted with ethyl acetate, the organic phase is dried with anhydrous sodium sulfate, filtered, and distilled under reduced pressure After the solvent was removed, 124 mg of a red solid was obtained by separation on a silica gel column with a yield of 60%. It was identified as the target compound by NMR, and the trans compound was the main one.

[0033] 1 H NMR (400MHz, CDCl 3 )δ7.29-7.38(m, 5H), 7.09(d, J=8.0Hz, 2H), 6.82(d, J=8.0Hz, 2H), 6.08(s, 1H), 4.86(d, J=7.8 Hz, 1H), 4.81(d, J=15.1Hz, 1H)...

Embodiment 2

[0035]

[0036] Under nitrogen protection at room temperature, 170 mg of raw materials, 113 mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), 6 mL of 1,4-dioxane and 0.6 mL of water were added to a 25 mL three-neck flask to prepare into a reaction solution. Heated to reflux, the reaction solution was a brown solution. Use TLC to track the reaction to the end, cool to room temperature, add 10mL saturated sodium bicarbonate solution to the reaction solution, extract with 20mL ethyl acetate, combine the organic phases, wash the organic phase twice with 20mL water, dry over anhydrous sodium sulfate, reduce After the ethyl acetate was evaporated under pressure, it was separated and purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain 116 mg of a colorless oily compound with a yield of 79%, which was identified as the target compound by NMR.

[0037] 1 H NMR (400MHz, CDCl 3 )δ7.22-7.39(m, 7H), 6.88(d, J=8.2Hz, 2H), 5.42(t, J=8.2Hz, 1H), 4.54(d,...

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Abstract

The invention provides a synthesizing method of an oxazolidine compound. In the method, a phenylethylamine derivative performs oxidation to prepare the oxazolidine compound by virtue of an organic oxidant, wherein the organic oxidant is one of benzoquinone oxidant, hypervalent iodide oxidant or halogenated imide oxidant. The product prepared by the method is an important bioactive substance, and plays an important role in medicament synthesis and application; and compared with the prior art, the synthesizing method has the characteristics of mild condition, wide raw material practicality, high yield, easily available reaction raw materials, is simple in operation and the like, and is suitable for laboratory preparation and industrial scale production.

Description

technical field [0001] The invention relates to a synthesis method of an oxazolidinone compound, in particular to a synthesis method of an oxazolidinone compound using an organic oxidant. Background technique [0002] Oxazolidinone compounds are important biologically active substances, which play a very important role in the synthesis and application of drugs. [0003] At present, the method for synthesizing oxazolidinone compound mainly contains: in the mixed solvent of water and acetonitrile, use the mixed system of potassium persulfate and copper sulfate to carry out oxidation reaction and generate oxazolidinone compound (such as: Tetrahedron Letter, 1988,29 , 5177-5180; Japanese patent, JP 1-228946); in the mixed solution of water and acetone, use cerium ammonium nitrate and divalent cupric salt as oxidizing agent, prepare oxazolidinone compound (Japanese patent, JP 8 -231518); [0004] In the existing methods for preparing oxazolidinone compounds, inorganic oxidizing...

Claims

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Application Information

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IPC IPC(8): C07D263/24
Inventor 许羚陈文杰李平筒井英之
Owner TORAY FIBER RES INST(CHINA) CO LTD
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