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A kind of preparation method of 3-tert-butoxyamido-4,4,4-trifluorobutyric acid methyl ester

A technology of tert-butoxyamido and methyl trifluorobutyrate, which is applied in the field of preparation of 3-tert-butoxyamido-4,4,4-methyl trifluorobutyrate, can solve the problem of harsh reaction conditions and raw materials. The problems of high price and many by-products can achieve the effect of low reaction temperature, easy availability of raw materials and easy operation.

Active Publication Date: 2016-01-20
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages: low reaction conversion rate, many by-products, large amount of waste liquid
[0006] 2) This method adopts ammonia as a raw material, and reacts under high temperature and high pressure conditions, and the reaction conditions are not easy to satisfy
Disadvantages: 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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  • A kind of preparation method of 3-tert-butoxyamido-4,4,4-trifluorobutyric acid methyl ester
  • A kind of preparation method of 3-tert-butoxyamido-4,4,4-trifluorobutyric acid methyl ester
  • A kind of preparation method of 3-tert-butoxyamido-4,4,4-trifluorobutyric acid methyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] At -20°C, methyl 4,4,4-trifluoro-3-oxobutyrate (1.701g, 0.01mol) was added to the organic solvent ether (8.5ml), and then triethylamine (1.012g ,0.01mol), acetic anhydride (1.021g, 0.01mol), and then add tert-butyl carbamate (1.172g, 0.01mol); the reaction was slowly raised to 20°C (3-5°C / min), and kept for 1h; Filtrate, concentrate the filtrate under normal pressure to obtain a white solid; dry in a vacuum oven at 40°C for 6 hours, add the dried product from the previous step to an autoclave, add 8.5ml of methanol solvent to dissolve, then add 0.0085g of palladium carbon catalyst, hydrogenation For reduction, the temperature is 30° C., and the reaction time is 4 hours. After the reduction is completed, filter, and the filtrate is distilled off the solvent under normal pressure to obtain the product. The yield is 80%, and the purity detected by gas chromatography is 99%. Product melting point: 60~62℃.

Embodiment 2

[0026] At 0°C, methyl 4,4,4-trifluoro-3-oxobutyrate (1.701g, 0.01mol) was added to the organic solvent ether (17ml), and then triethylamine (5.060g, 0.05 mol), acetic anhydride (5.105g, 0.05mol), and then add tert-butyl carbamate (8.505g, 0.05mol); slowly raise the reaction to 50°C (3-5°C / min), keep the reaction for 4h; filter, Concentrate the filtrate under normal pressure to obtain a white solid; dry it in a vacuum oven at 40°C for 6 hours, add the dried product from the previous step to an autoclave and add 17ml of methanol solvent to dissolve, then add 0.085g of palladium carbon catalyst, hydrogenation reduction, temperature The temperature is 60°C, the reaction time is 8h, after the reduction is completed, filter, and the filtrate is distilled off the solvent under normal pressure to obtain the product. The yield is 95%, and the purity detected by gas chromatography is 99.3%.

Embodiment 3

[0028] At -10°C, methyl 4,4,4-trifluoro-3-oxobutyrate (1.701g, 0.01mol) was added to the organic solvent tetrahydrofuran (10.2ml), and then pyridine (1.582g, 0.02 mol), acetic anhydride (2.042g, 0.02mol), then add tert-butyl carbamate (2.344g, 0.02mol); slowly raise the reaction to 30°C (3~5°C / min), keep the reaction for 2h; filter, Concentrate the filtrate under normal pressure to obtain a white solid; dry it in a vacuum oven at 40°C for 6 hours, add the dried product from the previous step to an autoclave and add 10.2ml of ethanol solvent to dissolve it, then add 0.017g of palladium carbon catalyst, hydrogenation and reduction, The temperature is 40°C, the reaction time is 5h, after the reduction is completed, filter, and the filtrate is distilled off the solvent under normal pressure to obtain the product. The yield was 83.3%, and the purity detected by gas chromatography was 99.6%.

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Abstract

The invention discloses a method for preparing 3-tert-butyl oxanamide-4,4,4-trifluoro-methyl butyrate, belonging to the technical field of organic synthesis. The method comprises the following steps: adding 4,4,4-trifluoro-3-oxymethyl butyrate into an organic solvent at -20 to 0 DEG C, adding alkali and a dehydrating agent, further adding carbamic acid tert-butyl ester, slowly (3-5 DEG C / minute) heating to be 20-50 DEG C when the components are reacted, performing thermal reaction for 1-4 hours, filtering, concentrating the filtrate at normal pressure so as to obtain a white solid, drying in a vacuum oven at 40 DEG C for 6 hours, adding the dried product into a high pressure kettle, adding a solvent to dissolve the product, adding a catalyst, performing hydrogenation reduction for 4-8 hours at 30-60 DEG C, filtering after the reaction is completed, and distilling out the solvent from the filtrate at normal pressure, thereby obtaining a product. The yield is 80-95%, and the gas chromatography detection purity is greater than 99.0%. By adopting the method, the raw materials are cheap and easy to obtain, the reaction temperature is low, the time is short, and reagents such as a fluorinating reagent with harsh conditions are avoided.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 3-tert-butoxyamido-4,4,4-trifluorobutyric acid methyl ester. Background technique [0002] 3-tert-butoxyamido-4,4,4-trifluorobutyric acid methyl ester is an important pharmaceutical raw material, especially the raw material of polypeptide drugs for the treatment of tumors and AIDS. There are many methods reported in its synthesis literature, mainly including: [0003] 1) This method uses a four-step synthesis method: imidization, double bond transfer, acidification and basification, and amidation. Disadvantages: low reaction conversion rate, many by-products, and large amount of waste liquid. [0004] Reaction equation: [0005] [0006] 2) In this method, ammonia gas is used as a raw material, and the reaction is carried out under high temperature and high pressure conditions, and the reaction conditions are difficult to satisf...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/22C07C269/06
Inventor 王大明王春博管月陈春海党国栋赵晓刚周宏伟
Owner JILIN UNIV
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