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A kind of preparation method of 3-(substituted/non-substituted phenyl)-3-hydroxypropionylhydroxamic acid

A technology of hydroxypropionyl hydroxamic acid and ethyl hydroxypropionate is applied in the field of preparation of aryl propionyl hydroxamic acid compounds, and can solve the problems such as inability to be applied in practical production, expensive ethyl bromoacetate, increased operational complexity, and the like, Achieve the effect of optimizing the synthesis route, improving the total yield and reducing the preparation cost

Active Publication Date: 2021-01-15
JISHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method cannot be applied to the actual production
In the first step of preparation, on the one hand, the raw material ethyl bromoacetate is relatively expensive and the production cost is high; on the other hand, the zinc powder needs to be activated before participating in the reaction, which increases the complexity of the operation. only 41%
In the final step of synthetic target product 3-(substituted / non-substituted phenyl)-3-hydroxy propionylhydroxamic acid, used excessive hydroxylamine hydrochloride and excessive sodium methylate, but excessive sodium methylate in the reaction solution will Cause many side reactions, greatly excessive hydroxylamine hydrochloride can produce a large amount of NaCl, this not only causes the waste of raw material but also increases production cost (comprising three waste treatment costs), simultaneously this step reaction yield is not high (being 76%) , there is still a large room for productivity improvement

Method used

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  • A kind of preparation method of 3-(substituted/non-substituted phenyl)-3-hydroxypropionylhydroxamic acid
  • A kind of preparation method of 3-(substituted/non-substituted phenyl)-3-hydroxypropionylhydroxamic acid
  • A kind of preparation method of 3-(substituted/non-substituted phenyl)-3-hydroxypropionylhydroxamic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: Preparation of intermediate 3-(3-chlorophenyl) ethyl propionate-3-ketone (Ⅳ)

[0050] Dissolve 141.6 grams of diethyl carbonate in 1000 mL of 1:1 ethanol-tetrahydrofuran (THF), add 12.4 grams of catalyst 1 Amberlite IRA-400 under stirring, heat up to 45 °C, and dissolve 154.5 grams of m-chloroacetophenone in 1000 mL of the above ethanol -THF mixed solvent was added dropwise within 1h, continued to stir for 6h, filtered and recovered Amberlite IRA-400, AmberliteIRA-400 was washed 3 times with the above ethanol-THF mixed solvent, the filtrates were combined, most of the solvent was evaporated, and added under stirring 1500mL water, CH 2 Cl 2 Extraction, washed with saturated brine to neutral, anhydrous MgSO 4 Dry, filter, evaporate the solvent, and distill under reduced pressure to obtain 204 g of colorless oily liquid 3-(3-chlorophenyl) ethyl propionate-3-one, with a yield of 90%;

Embodiment 2

[0051] Embodiment 2: by the similar method of embodiment 1, from solvent type, catalyst type and material ratio reaction condition has been studied, research results are shown in Table 1.

[0052] Table 1 yields of compound IV under various reaction conditions.

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059] Note: Other conditions of the above research: reaction temperature 60°C; reaction time TLC traced until m-chloroacetophenone was reacted or reacted for 48 hours; catalyst dosage was calculated according to m-chloroacetophenone.

[0060] As can be seen from the table:

[0061] 1. For most catalysts, the three solvents of methanol, ethanol and ethanol-THF are beneficial to the reaction. In many cases, the yield can exceed 50%, especially when ethanol-THF is used as the solvent, the yield can reach up to 87% ; Solvents such as ether and water are unfavorable to the reaction.

[0062] 2. As for the catalyst, NaOH and NaOEt, which are commonly...

Embodiment 3

[0065] Embodiment 3: the preparation of intermediate 3-(3-chlorophenyl)-3-hydroxypropionic acid ethyl ester (Ⅴ)

[0066] Dissolve 226.5 g of 3-(3-chlorophenyl) ethyl propionate-3-one in 1500 mL of ethanol, add 80 mL of glacial acetic acid, and feed H under stirring. 2 Remove the air in the reaction system, add 11.3 grams of Pd-C, heat up to 40 ° C, continue to 2 React under the atmosphere for 6 hours, filter, recover the catalyst, and evaporate the solvent under reduced pressure to obtain a light yellow oily substance, ethyl 3-(3-chlorophenyl)-3-hydroxypropionate, with a yield of 92%.

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Abstract

The invention discloses a preparation method of 3-(substituted / non-substituted phenyl)-3-hydroxy propionyl hydroxamic acid. Diethyl carbonate and acetophenone or acetophenone derivatives thereof are used as starting raw materials; through three-step reaction, the preparation of 3-(substituted / non-substituted phenyl)-3-hydroxy propionyl hydroxamic acid is realized. The synthetic route is optimized;the reaction conditions and the catalysts are carefully designed; the total yield is greatly improved; the reaction is mild; the operation is simple; the cheap raw materials and the green and environment-friendly process are used; the preparation cost is greatly reduced.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a preparation method of a class of aryl propionyl hydroxamic acid compounds. [0002] technical background [0003] Human infection with bacteria such as Helicobacter pylori, Proteus vulgaris, Proteus mirabilis, and Ureaplasma urealyticum can cause gastritis, gastric ulcer, duodenal ulcer, gastric Atrophy, intestinal metaplasia, gastric cancer, gastric lymphoma, kidney stones, bladder stones and other diseases. The pathogenic cause of these bacteria is that they can produce urease, which can hydrolyze the metabolite urea in the body to produce ammonia. In the stomach, ammonia will affect the permeability of the gastric mucosa and produce toxicity to the gastric parietal cells, causing gastric diseases such as ulcers , In the urinary system, ammonia will alkalinize the urine, leading to the precipitation of calcium and magnesium plasma in the urine to form...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/732C07C67/31C07C67/343C07C69/738C07C259/06
CPCC07C67/31C07C67/343C07C259/06C07C69/738C07C69/732
Inventor 肖竹平李崴一倪伟伟刘佳佳
Owner JISHOU UNIVERSITY
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