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Preparation method of N-[2-(3,4-dimethoxy phenyl)-2-oxo-ethyl]-2-(3,4,5-trimethoxy phenyl) acetamide

A technology of trimethoxyphenyl and dimethoxyphenyl, applied in the field of organic chemical synthesis, can solve problems such as low yield, and achieve the effects of high yield, simple process and easy preparation

Inactive Publication Date: 2014-03-26
杨晓丽
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Problems solved by technology

However, in the Gabriel reaction, hydrazine hydrazine hydrolysis is required to obtain the primary a

Method used

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Embodiment 1

[0009] Example 1: Add 0.5g 3,4-dimethoxy-1-aminoacetylbenzene hydrobromide, 0.41G 3,4,5-trimethoxyphenylacetic acid, 0.55g DMAP and 35mL into the reaction flask Anhydrous dichloromethane, cool to 0°C, add 0.38g EDCI·HCl under nitrogen protection. After stirring the reaction for 30 minutes, the temperature was raised to room temperature, and the stirring reaction was continued for 24 hours. Then it was washed with 50 mL of 2.0 mol / L hydrochloric acid, 50 mL of saturated sodium bicarbonate solution, 50 mL of saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from dichloromethane-ethyl acetate to obtain 0.55 g (1.36 mmol) of compound N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl Yl]-2-(3,4,5-trimethoxyphenyl)acetamide, white solid, yield 76%.

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Abstract

The invention discloses a preparation method of N-[2-(3,4-dimethoxy phenyl)-2-oxo-ethyl]-2-(3,4,5-trimethoxy phenyl) acetamide. The preparation method comprises the following steps: (1) adding 3,4,5-dimethoxy-1-aminoacetyl phenyl hydrobromide, 3,4,5-trimethoxy phenylacetate, DMAP (dimethylaminopyridine) and anhydrous dichloromethane in a reaction flask, cooling to 0 DEG.C, adding EDCI.HCl under the nitrogen protection, stirring to react for 30 minutes, and then warming to room temperature, and continuously stirring to react for 24 hours; (2) orderly washing by using 2.0mol/L hydrochloric acid, a saturated sodium bicarbonate solution and a saturated saline solution, drying by using anhydrous sodium sulfate, removing the solvent through reduced pressure evaporation, and recrystallizing residue by using dichloromethane-ethyl acetate to obtain the N-[2-(3,4-dimethoxy phenyl)-2-oxo-ethyl]-2-(3,4,5-trimethoxy phenyl) acetamide. The preparation method has the advantages that the method is simple and convenient, and the yield can achieve 76%.

Description

Technical field [0001] The invention belongs to the technical field of organic chemistry synthesis, and specifically relates to a N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-2-(3,4,5-trimethoxy (Phenyl) acetamide preparation method. Background technique [0002] Combretastatin is a natural product with anticancer activity isolated from the South African bush (Combretum caffrum). It inhibits tubulin polymerization and selectively prevents blood flow to the tumor, leading to the death of tumor cells. The purpose of anti-cancer. Among these natural products, Combretastatin A4 (CA-4) has the highest activity and has a strong inhibitory effect on a variety of tumors. Because CA-4 has poor water solubility and low bioavailability, it is phosphorylated into a water-soluble disodium phosphate prodrug (CA-4P), which greatly improves its anti-tumor activity in vivo. CA-4 disodium phosphate has entered the phase III clinical research phase. However, CA-4 has the disadvantage of isomerizing f...

Claims

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Application Information

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IPC IPC(8): C07C235/34C07C231/02
Inventor 杨晓丽韦丽
Owner 杨晓丽
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