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Chiral monomer containing L-amino acid group

A chiral monomer, amino acid-based technology, applied in the field of 1-substituted-2-methoxy-2-oxoethylacrylamide, can solve problems such as limited application

Inactive Publication Date: 2011-07-20
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such amino acid derivatives are generally grafted on SiO 2 On the surface of support materials such as polyester or resin, there are not many chiral monomers that are reactive in themselves, which limits the application of such compounds in chiral resolution materials.

Method used

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  • Chiral monomer containing L-amino acid group
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  • Chiral monomer containing L-amino acid group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of L-leucine chiral monomer:

[0020] Add 35mL of methanol into a 100mL three-necked flask (installed with tail gas absorption device), slowly add 3.3mL of thionyl chloride dropwise under ice bath (the temperature is controlled below 0°C), and stir for 1h. Add 5.0g of L-leucine, react at room temperature for 3h, then gradually raise the temperature to 65°C and reflux for 3h. Evaporate methanol and excess thionyl chloride, and precipitate white needle-like crystals after cooling. Suction filter and dry to obtain white needle-like L-leucine methyl ester hydrochloride.

[0021] Take 2.0g of L-leucine methyl ester hydrochloride in 15mL of N,N-dimethylformamide (DMF), and dissolve it by ultrasonic. 4 mL of triethylamine was added, and 1.13 mL of acryloyl chloride was slowly added dropwise in an ice bath. After the addition, the temperature was raised to 70°C and refluxed for 2h. After the reaction was completed, 50 mL of water was added, extracted three times ...

Embodiment 2

[0023] Preparation of L-alanine chiral monomer:

[0024] Reaction process is with embodiment 1. 1 H NMRδ (ppm): 1.21 (d, 3H), 4.31 (m, 1H), 3.58 (s, 3H), 5.53 (dd, 1H), 6.01 (d, 1H), 6.58 (d, 1H), 8.98 ( s, 1H).

Embodiment 3

[0026] Preparation of L-valine chiral monomer:

[0027] Reaction process is with embodiment 1. 1 H NMRδ (ppm): 1.21 (s, 6H), 2.49 (m, 1H), 4.31 (m, 1H), 3.48 (s, 3H), 5.03 (dd, 1H), 6.21 (d, 1H), 6.38 ( d, 1H), 9.08 (s, 1H).

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Abstract

The invention discloses a chiral monomer containing an L-amino acid group. The structure of the monomer is shown in the specifications, wherein R is -CH3. The chiral monomer is obtained by esterifying L-amino acids such as L-leucine and the like serving as starting raw materials and methanol and further condensing with acrylic acid. The structure of the chiral monomer has the characteristics of an L-amino acid chiral group and acryloyl CH2=CH-C0-, the L-amino acid chiral group can endow a material with a chiral recognition characteristic, and C=C double bonds undergo a free radical copolymerization reaction with other monomers containing the C=C double bonds to prepare a chiral high polymer material.

Description

technical field [0001] The invention relates to a class of chiral monomers containing L-amino acid groups, specifically 1-substituted-2-methoxy 2-oxoethylacrylamide. This kind of chiral monomer structure contains L-amino acid chiral group and acryloyl CH 2 =CH-CO-characteristics, the L-amino acid chiral group can endow the material with chiral recognition characteristics, and the C=C double bond facilitates free radical copolymerization of monomers with other monomers containing C=C double bonds. Used to prepare chiral polymer materials. Background technique [0002] In recent years, with the continuous increase of the market share of chiral drugs and the deepening of people's understanding of the safety of chiral drugs, the research and development of chiral resolution technology and resolution materials has become a hot field in the research and development of new drugs in the world today. [0003] At present, the most common chiral separation materials are mainly the ch...

Claims

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Application Information

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IPC IPC(8): C07C233/31C07C231/02C07C321/14C07C319/20C07D207/09C07D209/20C07B53/00C08F220/58C08F220/60
Inventor 陈娇娇刘鑫杜显丽王乐乐张丹丹陈莉
Owner TIANJIN POLYTECHNIC UNIV
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