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Preparation method of methyl trifluoroalaninate

A technology of methyl trifluoroalanine and methyl trifluoropyruvate, which is applied in the field of organic synthesis, can solve the problems of sodium azide being inflammable and explosive, no economical and effective report, harsh reaction conditions, etc., and achieves easy operation. , the effect of short time and low reaction temperature

Inactive Publication Date: 2015-03-04
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] 2) This method uses sodium azide as a raw material. Although there are few steps, sodium azide is flammable and explosive
Disadvantages of this method: harsh reaction conditions, low conversion rate, high raw material price and not easy to obtain
[0009] Currently there is no cost-effective and easy-to-operate report

Method used

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  • Preparation method of methyl trifluoroalaninate
  • Preparation method of methyl trifluoroalaninate
  • Preparation method of methyl trifluoroalaninate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] At 0°C, methyl trifluoropyruvate (15.6 g, 0.1 mol) and 15.6 mL of toluene were added to a four-necked flask, sodium acetate (8.2 g, 0.1 mol), and hydroxylamine hydrochloride (6.9 g, 0.1 mol) were added. The reaction was slowly heated to reflux (about 110 degrees), and the reaction was kept for 1 hour. The temperature of the reaction solution was lowered to 30 degrees, p-toluenesulfonic acid (1.7g, 0.01mol) was added, heated to reflux (110°C), and reacted for 1 hour. After the toluene was distilled off under reduced pressure, the reaction liquid was poured into a mixture of ice and water, and a large amount of solid was precipitated, which was filtered. After the filtered solid was dried at 50°C for 10 hours, it was added to the autoclave, 0.078g of palladium carbon catalyst was added, 78ml of ethanol was added to dissolve, hydrogenation reduction, 20°C, react for 3 hours, filter after the completion of the reaction, the filtrate is always The solvent is distilled off un...

Embodiment 2

[0025] At 15℃, add methyl trifluoropyruvate (15.6g, 0.1mol) and 78.0mL xylene into a four-necked flask, add sodium hydroxide (12.0g, 0.3mol), hydroxylamine hydrochloride (20.7g, 0.3mol) . The reaction was slowly heated to reflux (about 130 degrees), and the reaction was kept for 2 hours. The reaction solution was cooled to 30 degrees, and p-toluenesulfonic acid (5.1g, 0.03mol) was added, heated to reflux (130°C), and reacted for 2h. After the xylene was distilled off under reduced pressure, the reaction liquid was poured into a mixture of ice and water, and a large amount of solid was precipitated, which was filtered. After the filtered solid was dried at 50°C for 10 hours, added to the autoclave, added 0.078 g of catalyst palladium carbon, added 78 ml of methanol to dissolve, hydrogenated reduction, 50°C, reacted for 4 hours, filtered after the reaction is complete, the filtrate is usually The solvent is distilled off by pressure, the obtained crude product is distilled unde...

Embodiment 3

[0027] At 30℃, add methyl trifluoropyruvate (15.6g, 0.1mol) and 124.8mL methyl acetate into a four-necked flask, add sodium bicarbonate (42.0g, 0.5mol), hydroxylamine hydrochloride (34.5g, 0.5mol) ). The reaction was slowly heated to reflux (approximately 57 degrees), and the reaction was kept for 4 hours. The reaction solution was cooled to 30 degrees, and p-toluenesulfonic acid (8.5g, 0.05mol) was added, heated to reflux (57°C), and reacted for 4h. After the methyl acetate was distilled off under reduced pressure, the reaction liquid was poured into a mixture of ice and water, and a large amount of solid was precipitated, which was filtered. After the filtered solid was dried at 50°C for 10 hours, it was added to the autoclave, 0.78 g of palladium carbon catalyst was added, and 156 ml of ethyl acetate was added to dissolve it. Hydrogenation reduction was carried out at 80°C for 5 hours. After the reaction was completed, it was filtered. The solvent is evaporated from the fi...

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Abstract

The invention relates to a preparation method of methyl trifluoroalaninate, belonging to the technical field of organic synthesis. The preparation method comprises the following steps: dissolving methyl trifluoropyruvate in an organic solvent at 0-30 DEG C, adding alkali, hydroxylamine hydrochloride and p-toluenesulfonic acid, heating until reflux, carrying out vacuum distillation to remove the solvent, pouring the crude product into an ice water mixture, precipitating abundant solid, filtering, and drying; and adding the product into a high-pressure autoclave, adding an organic solvent for dissolution, adding a catalyst, carrying out hydrogenation reduction, filtering, distilling the filtrate under ordinary pressure to remove the solvent, and carrying out vacuum distillation on the crude product to obtain the end product methyl trifluoroalaninate. The technical line is reasonably selected, is simple and convenient, and is easy to operate; the invention technically provides a successful synthesis method for synthesizing the intermediate of methyl trifluoroalaninate; and the method has the advantages of cheap and accessible raw materials, low reaction temperature and short time, and avoids using the fluoridation reagent and other reagents requiring harsh conditions. The yield of the end product is 93-97%, and the purity is greater than 99.0%.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for preparing trifluoroalanine methyl ester. Background technique [0002] Trifluoroalanine methyl ester is an important raw material for drugs, especially for the treatment of tumors and AIDS peptide drugs. There are many other methods reported in the literature, including: [0003] 1) This method uses a three-step synthesis: imidization, double bond transfer, and alkalization after acidification. The main disadvantages of this method are low reaction conversion rate, large by-products, and large amount of waste liquid. [0004] Reaction equation [0005] [0006] 2) This method uses sodium azide as a raw material. Although there are few steps, sodium azide is flammable and explosive. Disadvantages of this method: harsh reaction conditions, low conversion rate, high price of raw materials and not easy to obtain. [0007] Reaction equation [0008] [0009] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/20C07C227/04
Inventor 王大明姜勃弛管月陈春海党国栋赵晓刚周宏伟
Owner JILIN UNIV
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