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Method for synthesizing 2-hydroxy-3-alkoxy propionate compounds

A compound, methyl technology, applied in the synthesis of 2-hydroxy-3-alkoxy propionate compounds, the field of endothelin receptor inhibitor intermediates, can solve problems such as discomfort, toxic irritation and strong corrosiveness , to achieve a wide range of applications, easy industrial production, easy to operate

Active Publication Date: 2015-06-10
天津药物研究院药业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, a preparation method of 2-hydroxy-3-alkoxy propionate is disclosed in Journal of Medicinal Chemistry, 1996, vol.39, #11p.2123-2128, which uses Lewis acid BF 3 .Et 2 O or p-toluenesulfonic acid catalyzes the action of 2,3-epoxypropionate compounds and alcohols to achieve the ring-opening effect of epoxy compounds, but BF 3 .Et 2 O is a flammable, toxic, highly irritating and highly corrosive reagent, and it is easy to decompose in humid air to produce highly toxic hydrogen fluoride fumes. Although this method is suitable for laboratory research, it is not suitable for the implementation of industrial scale-up

Method used

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  • Method for synthesizing 2-hydroxy-3-alkoxy propionate compounds
  • Method for synthesizing 2-hydroxy-3-alkoxy propionate compounds
  • Method for synthesizing 2-hydroxy-3-alkoxy propionate compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Dissolve 600 grams of methyl 3,3-diphenyl-2,3-epoxypropionate in 2.4 liters of anhydrous isopropanol, stir at 20°C, slowly add 48 grams of hydrochloric acid, keep the system temperature after adding After stirring for 1 hour at 20°C, add 4.8 liters of water, continue to stir for half an hour, filter with suction, separate the solid product, and dry it in vacuum at 50°C to obtain 2-hydroxy-3-isopropoxy-3,3-diphenyl methyl propionate.

[0035] Yield: 95.5%

[0036] HPLC purity: 99.7%

Embodiment 2

[0038] Dissolve 10 kg of ethyl 3,3-diphenyl-2,3-epoxypropionate in 120 liters of anhydrous methanol, stir at 25°C, slowly add 2 kg of hydrochloric acid, and keep the system temperature at 30 ℃, stirred for 1 hour, added 150 liters of water, stirred for 2 hours, discharged, filtered, and the filter cake was vacuum-dried at 50°C to obtain 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid ethyl ester.

[0039] Yield: 96.2%

[0040] HPLC purity: 99.3%

Embodiment 3

[0042] Dissolve 450 grams of 3,3-diphenyl-2,3-glycidylpropionate in 2.7 liters of absolute ethanol, stir at 30°C, slowly add 80 grams of hydrochloric acid, after the addition is complete, keep the temperature at 40°C After stirring for 1.5 hours, add 3 liters of water, stir for 0.5 hours, filter with suction, and dry the filter cake under vacuum at 50°C to obtain propyl 2-hydroxy-3-ethoxy-3,3-diphenylpropionate.

[0043] Yield: 95.7

[0044] HPLC purity: 99.1%

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Abstract

The invention relates to the technical field of medical intermediates and particularly relates to a method for synthesizing 2-hydroxy-3-alkoxy propionate compounds. The method comprises the step of carrying out ring opening on 2,3-epoxy acrylate compounds and C1-C3 chain saturated monohydric alcohol serving as a reaction solvent in the presence of gaseous hydrogen chloride or a water solution of gaseous hydrogen chloride, so as to prepare the synthesizing 2-hydroxy-3-alkoxy propionate compounds. The method is safe, free of toxic, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical intermediates. Specifically, the present invention relates to an endothelin receptor inhibitor intermediate, in particular to a method for synthesizing 2-hydroxy-3-alkoxy propionate compounds. Background technique [0002] Endothelin is a peptide composed of 21 amino acids that is synthesized and released by the endothelium of blood vessels. Endothelin is a potent vasoconstrictor and has a strong effect on vascular tone. Elevated or abnormal endothelin release causes sustained vasoconstriction in peripheral, renal, and cerebral vessels that can lead to disease. Increased plasma levels of endothelin have been found in patients with hypertension, myocardial infarction, cerebrovascular hypertension, Raynaud's syndrome, atherosclerosis and respiratory spasm. Substances which specifically inhibit the binding of endothelin to receptors should therefore also antagonize the various physiological...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/734
CPCC07C67/31C07C69/734
Inventor 魏群超刘长鹰石玉张海枝刘鹏李祎亮徐为人邹美香汤立达
Owner 天津药物研究院药业有限责任公司
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