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Method for synthesizing 4-(hydroxymethyl)-5-methyl-[1, 3] dioxol-2-one

A technology of dioxole and hydroxymethyl is applied in the field of synthesizing 4--5-methyl-[1,3]dioxol-2-one, and can solve the problem of low yield of target product and other problems, to achieve a more complete reaction, improve the reaction rate and yield, and maintain consistency.

Active Publication Date: 2020-09-11
河南省三生药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method reduces the extraction steps, it needs to add a catalyst, and the target product yield is relatively low, only 76.5%

Method used

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  • Method for synthesizing 4-(hydroxymethyl)-5-methyl-[1, 3] dioxol-2-one
  • Method for synthesizing 4-(hydroxymethyl)-5-methyl-[1, 3] dioxol-2-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Add DMDO-Cl (50g, 0.337mol), formic acid (46.5g, 1.01mol) and 1,2-dichloroethane (300g) sequentially into a 1000mL reaction flask, stir in an ice bath, and cool down to below 15°C , slowly add triethylamine (101g, 1.01mol) dropwise, after the addition is completed, heat up to reflux reaction, react for 4 hours, sample HPLC to monitor the reaction process, the reaction of raw materials is completed, stop the reaction, drop to room temperature, filter, filter cake with a small amount of Washed twice with ice 1,2-dichloroethane. Combine the filtrates, wash the filtrate twice with 200 mL of water, combine the organic phases, add an appropriate amount of anhydrous magnesium sulfate to dry, filter, and concentrate the filtrate to dryness to obtain 48.9 g of a concentrated ester intermediate.

[0037] (2) Add 250g of ethanol to the concentrate prepared in step (1), raise the temperature to 40°C, slowly add hydrogen chloride-ethanol solution (25% by volume, 25mL) dropwise, ...

Embodiment 2

[0040] (1) Add DMDO-CL (50g, 0.337mol), formic acid (23.3g, 0.5mol) and 1,2-dichloroethane (300g) sequentially into a 1000mL reaction flask, stir in an ice bath, and cool down to below 15°C , slowly add triethylamine (68.2g, 0.674mol) dropwise, after the dropwise addition is completed, heat up to reflux reaction, react for 10 hours, sample HPLC to monitor the reaction process, the reaction of raw materials is completed, stop the reaction, drop to room temperature, filter, filter cake with A small amount of ice 1,2-dichloroethane was washed twice. Combine the filtrates, wash the filtrate twice with 200 mL of water, combine the organic phases, add an appropriate amount of anhydrous magnesium sulfate to dry, filter, and concentrate the filtrate to dryness to obtain 47.88 g of a concentrated ester intermediate.

[0041] (2) Add 250g of ethanol to the concentrate prepared in step (1), raise the temperature to 40°C, slowly add hydrogen chloride-ethanol solution (25% by volume, 25mL)...

Embodiment 3

[0044](1) Add DMDO-Cl (50g, 0.337mol), formic acid (46.5g, 1.01mol) and dichloromethane (300g) in sequence in a 1000mL reaction flask, stir in an ice bath, cool down to below 15°C, and slowly add pyridine dropwise (79.1g, 1.0mol), dropwise completed, heated to reflux reaction, reacted for 6 hours, sampled HPLC to monitor the reaction process, the reaction of the raw materials was completed, stopped the reaction, cooled to room temperature, filtered, and the filter cake was washed with a small amount of ice dichloromethane for 2 Second-rate. Combine the filtrates, wash the filtrate twice with 200 mL of water, combine the organic phases, add an appropriate amount of anhydrous magnesium sulfate to dry, filter, and concentrate the filtrate to dryness to obtain 48.4 g of a concentrated ester intermediate.

[0045] (2) Add methanol (250g) to the concentrate obtained in step (1), raise the temperature to 40°C, slowly add hydrogen chloride-methanol solution (volume fraction 20%, 30mL)...

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Abstract

The invention discloses a method for synthesizing 4-(hydroxymethyl)-5-methyl-[1, 3] dioxol-2-one, and belongs to the technical field of chemical synthesis. The reaction equation in the synthesis process is as shown in the specification. According to the method, a proper solvent and a proper hydrolysis medium are selected, and the dosage ratio of reactants is optimized, so that the reaction rate and yield are greatly improved, the reaction is more complete and thorough, the yield of the target product is up to 92%, and the purity of the target product is up to 97%.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing 4-(hydroxymethyl)-5-methyl-[1,3]dioxol-2-one. Background technique [0002] Angiotensin II receptor antagonists are currently the first-line antihypertensive drugs, which have the advantages of clear curative effect, good antihypertensive effect, and small side effects. At the same time, it can prevent or treat circulatory system diseases, such as heart disease (cardiac hypertrophy, heart failure, myocardial infarction, etc.), nephritis, stroke, etc. [0003] Azilsartan medoxomil (Azilsartan, formula 1) is a potent and long-lasting angiotensin II receptor antagonist developed by Japan's Takeda Pharmaceutical Company. Angiotensin II receptor antagonist drugs for the treatment of hypertension are mostly used in the treatment of hypertension, and are currently the only angiotensin II receptor antagonist (sartan) drugs in the late cli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/40
CPCC07D317/40
Inventor 贾淑红吴斗灿朱文龙
Owner 河南省三生药业有限公司
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