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
1 Cites 0 Cited by

AI-Extracted 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 rat...
View more

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.

Application Domain

Organic chemistry

Technology Topic

Dimethyl formamideDichloroethane +11

Image

  • 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(9)

Example Embodiment

[0020] Example 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 vacuum for 24 hours to obtain the mixture of two kinds of optical isomers serine morpholine dione (i.e. BMMD I and BMMD II coexist Body), the product weight is 3.5g, and the productive rate is 29%.

Example Embodiment

[0022] Example 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 vacuum for 24 hours to obtain the mixture of two kinds of optical isomers serine morpholine dione (i.e. BMMD I and BMMD II coexist Body), the product weight is 4.0g, and the productive rate is 30%.

Example Embodiment

[0024] Example 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 vacuum for 24 hours to obtain a mixture of two optical isomers serine morpholine dione (i.e. BMMD I and BMMD II coexistence), the product weight is 4.55g, and the productive rate is 32.5%.

PUM

no PUM

Description & Claims & Application Information

We can also present the details of the Description, Claims and Application information to help users get a comprehensive understanding of the technical details of the patent, such as background art, summary of invention, brief description of drawings, description of embodiments, and other original content. On the other hand, users can also determine the specific scope of protection of the technology through the list of claims; as well as understand the changes in the life cycle of the technology with the presentation of the patent timeline. Login to view more.
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products