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Method for catalysis synthesis of (Z)-2-acetylamino methyl cinnamate through DCC/DMAP

A technology of methyl cinnamate and acetamido, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of complicated operation, only yield, high solubility and difficult to eliminate, and achieves simple post-processing. , the effect of easy industrial production

Inactive Publication Date: 2015-01-28
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, DMF was used as the solvent in the post-treatment, and after standing for 2 days, the impurity DCU (N,N'-dicyclohexylurea) was filtered out. Due to the high solubility of DCU in DMF, it is difficult to remove , to remove the solvent to obtain an oil, and then add an appropriate amount of methanol and ether with a volume ratio of 1:1 to freeze crystallization, and the obtained crystals can be recrystallized three times to obtain (Z)-2-Acetamidocinnamic acid methyl ester, the operation is cumbersome, and the yield rate is only 52%

Method used

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  • Method for catalysis synthesis of (Z)-2-acetylamino methyl cinnamate through DCC/DMAP
  • Method for catalysis synthesis of (Z)-2-acetylamino methyl cinnamate through DCC/DMAP

Examples

Experimental program
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Effect test

Embodiment

[0023] , Synthesis of 3-phenylacrylic acid azlactone (3)

[0024] Take 11.75 g of N-acetylaminoglycine, 5 g of sodium acetate, and 13.25 g of benzaldehyde into a 250 ml round-bottomed flask, then add 35 ml of acetic anhydride, reflux at 100 °C for 3 h, cool to room temperature, and precipitate a large amount of brown-yellow solid , placed in a refrigerator at 4°C overnight, filtered through a sand core funnel, washed with dilute acetic acid aqueous solution (20 ml×3), then washed with cold water until it was a yellow needle-like solid, and dried to obtain 13.65 g of a yellow compound 3 , and the yield was 73.8%.

[0025] 2. Preparation of (Z)-2-acetylaminocinnamic acid (4)

[0026] Transfer 13 g of the product obtained in the previous step to a 500 ml round bottom flask, add 50 ml of water, 100 ml of acetone, reflux at 80 °C for 4 h, evaporate to dryness with a rotary evaporator, add 200 ml of distilled water, heat to 100 °C and After hot suction filtration, the filtrate ...

Embodiment 2

[0035] Same as Example 1, but the volume ratio of the mixture of methanol and dichloromethane is 0.5:1, and the weight ratio of N,N-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) is 70:1. The yield was 68.0%, and the purity was greater than 99%.

Embodiment 3

[0037] Same as Example 1, but the volume ratio of the mixture of methanol and dichloromethane is 1:0.5, the weight ratio of N,N-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) is 90:1. The yield was 68.3%, and the purity was greater than 99%.

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Abstract

The present invention discloses a method for rapidly and efficiently preparing (Z)-2-acetylamino cinnamic acid and (Z)-2-acetylamino methyl cinnamate, and belongs to the field of organic chemistry. The method comprises: selecting low choice and easy availability benzaldehyde (1) and N-acetylglycine (2) as starting materials to obtain an intermediate 3-phenyl acrylic acid azlactone (3) under the effect of acetic anhydride and sodium acetate, carrying out a reflux reaction in an acetone and water mixed solution to obtain (Z)-2-acetylamino cinnamic acid (4), adding the methanol and methylene chloride mixed solution of the (Z)-2-acetylamino cinnamic acid (4) into the methanol solution of catalysts N,N-dicyclohexyl carbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) in a dropwise manner to carry out a reaction, and carrying out washing, extraction and recrystallization to obtain the target product. With the method, the high purity (Z)-2-acetylamino methyl cinnamate can be rapidly and efficiently obtained, the yield can be 68%, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of (Z)-methyl 2-acetylaminocinnamate, in particular to a method for synthesizing methyl (Z)-2-acetylaminocinnamate catalyzed by DCC / DMAP, which belongs to the field of organic chemistry. Background technique [0002] In the field of asymmetric catalytic hydrogenation, methyl (Z)-2-acetylaminocinnamate has been widely used as a standard substrate for the evaluation of chiral hydrogenation catalysts, new chiral ligands, water-soluble catalysts and immobilized chiral sex catalyst. At present, the prochiral substrate cannot be directly purchased in the market, and must be developed and prepared by itself, and the reaction requires chromatographic column separation and purification, which causes difficulties in the study of asymmetric catalytic hydrogenation reactions. Asymmetric catalytic hydrogenation is currently one of the most effective methods for the synthesis of chiral compounds. This method is very suita...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/47
Inventor 陈海涛段显英李非非王文新韩福娇付经国杨贯羽李继
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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