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Preparation method of two kinds of pure optical isomerism serine morpholine dione

A serine morpholine dione, optical isomerization technology, applied in the direction of organic chemistry, can solve the problems of optical stereo racemization, resolution, preparation of pure optical isomers, etc.

Inactive Publication Date: 2008-12-17
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] One of the purposes of the present invention is to solve the problem of optical stereo-racemization at the 6-position asymmetric carbon atom when the Serine morpholine diketone BMMD is synthesized by the Gongsha Weisi method, so that the two isomers in the synthesized serine morpholine dione The body content ratio is increased by more than two times (I / II≥2), in order to facilitate the resolution of the two isomers
The second object of the present invention is to solve the problem that the prior art cannot resolve two kinds of optically isomerized serine morpholine diketone mixtures (BMMD, I+II) and prepare pure optical isomers

Method used

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  • Preparation method of two kinds of pure optical isomerism serine morpholine dione
  • Preparation method of two kinds of pure optical isomerism serine morpholine dione

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add 500ml of DMF-DCE mixture (volume ratio DMF / DCE=2.0) and 6.7ml of Et in a 1000ml reactor 3 N, heat the reaction kettle to 60±1°C, add BPBS DMF-DCE mixture (16.0g BPBS dissolved in 133ml DMF and 67ml DCE mixture) dropwise to the kettle under stirring, and finish adding in 2 hours at constant temperature at 60±1°C , and then react at a constant temperature of 60±1°C for 18 hours. After the reaction, the DMF-DCE mixed solution was evaporated under reduced pressure, and the solid was added to acetate (500ml of methyl acetate) to obtain a solution, which was transferred to a separatory funnel, washed with water (to remove the precipitate), and the water was discarded. After washing the oil phase with distilled water three times, the oil phase was dried with anhydrous magnesium sulfate for 24 hours. Then the solvent of the liquid phase is evaporated under reduced pressure, and then recrystallized with methyl acetate, and the product is dried at room temperature under vacu...

Embodiment 2

[0023] Add 550ml of DMF-DCE mixture (volume ratio DMF / DCE=9.0) and 7.3ml of Et in the 1000ml reactor 3 N, heat the reaction kettle to 60±1°C, add BPBS DMF-DCE mixture (17.5g BPBS dissolved in 180ml DMF and 20ml DCE mixture) dropwise to the kettle under stirring, and finish adding in 2 hours at constant temperature at 60±1°C , and then react at a constant temperature of 60±1°C for 18 hours. After the reaction, the DMF-DCE mixed solution was evaporated under reduced pressure, and the solid was added to acetate (500ml of propyl acetate) to obtain a solution, which was transferred to a separatory funnel, washed with water (to remove the precipitate), and the water was discarded. After washing the oil phase with distilled water three times, the oil phase was dried with anhydrous magnesium sulfate for 24 hours. Then the solvent of the liquid phase is evaporated under reduced pressure, and then recrystallized with propyl acetate, and the product is dried at room temperature under va...

Embodiment 3

[0025] Add 580ml of DMF-DCE mixture (volume ratio DMF / DCE=1.0) and 7.7ml of Et in a 1000ml reactor 3N, heat the reaction kettle to 55±1°C, add BPBS DMF-DCE mixture (18.6g BPBS dissolved in 100ml DMF and 100ml DCE mixture) dropwise to the kettle under stirring, and finish adding in 2 hours at a constant temperature of 55±1°C. Then react at a constant temperature of 55±1° C. for 18 hours. After the reaction, the DMF-DCE mixed solution was evaporated under reduced pressure, and the solid was added to acetate (tert-butyl acetate 500ml) to obtain a solution, which was transferred to a separatory funnel, washed with water (to remove the precipitate), and discarded. The water phase and the oil phase were washed three times with distilled water, and then dried over anhydrous magnesium sulfate for 24 hours. Then the solvent of the liquid phase is evaporated under reduced pressure, and then recrystallized with tert-butyl acetate, and the product is dried at room temperature under vacuu...

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Abstract

The invention discloses a preparing method of two-pure optical isomeric serine morpholinedione compound, which is characterized by the following: adopting N-(2-bropropionyl)-O-benzyl serine as raw material; setting dimethyl formamide and 1, 2-dichloroethanes compound as reacting solvent to prepare BMMD,I+II; controlling the cyclization reacting temperature at 50-75 Deg C; reducing optical steric racemic degree of 6-position asysmetrical carbon atom.

Description

【Technical field】: [0001] The present invention relates to novel medical biodegradable polymers—two kinds of optically isomeric morpholinodione monomers (scientific name: 3-benzyloxymethyl-6-methyl-2,5-) used in the synthesis of poly(serine-lactic acid) Morpholine dione, hereinafter referred to as: serine morpholine dione, English abbreviation: BMMD) preparation method. 【Background technique】: [0002] In recent years, with the rapid development of medicine and biological tissue engineering science, the demand for medical biodegradable materials with excellent biocompatibility and biosafety is increasing rapidly at home and abroad. The polymer prepared by catalytic ring-opening polymerization using serine morpholine dione as a monomer can obtain a copolymer of serine and lactic acid—poly(serine-lactic acid), which is a new type of biological agent with excellent performance. degraded polymers. Nankai University Institute of Polymer Chemistry and "Ministry of Education Key ...

Claims

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Application Information

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IPC IPC(8): C07D265/32
Inventor 李弘张来东
Owner NANKAI UNIV
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