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Compound 2-methylol-3-substituted phenyl propionic acid with optical activity and its resolving process

A technology of phenylpropionic acid and optical activity, applied in the field of chemistry, can solve problems such as being unsuitable for industrialized production, cumbersome steps, rising cost, etc., and achieve the effects of good splitting efficiency, low price, and easy recovery

Active Publication Date: 2007-03-21
SHANGHAI SHYNDEC PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The general steps in the operation of the reported fasidotril synthesis method are relatively cumbersome, and the cost of the raw materials and catalysts used is relatively high, which makes the cost of the product relatively high, and is not suitable for industrial production.

Method used

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  • Compound 2-methylol-3-substituted phenyl propionic acid with optical activity and its resolving process
  • Compound 2-methylol-3-substituted phenyl propionic acid with optical activity and its resolving process
  • Compound 2-methylol-3-substituted phenyl propionic acid with optical activity and its resolving process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 4.0g (17.9mmol) of 2-hydroxymethyl-3-(3,4-methylenedioxy)phenylpropionic acid and 3.5g (17.9mmol) of meglumine into a 250ml single-necked bottle, add 60ml of ethanol, After reflux for 10 minutes, it was naturally cooled to room temperature, allowed to stand for 2 days, and 3.6 g of solid was obtained by filtration. Then recrystallized once with 100ml of ethanol to obtain 3.3g of solid.

[0032] Add 50ml of water to the solid, adjust the pH to 9 with 10% NaOH aqueous solution while stirring, filter, adjust the pH to 2 with 10% dilute hydrochloric acid in the filtrate, extract with 80ml ethyl acetate, dry over anhydrous sodium sulfate, and concentrate. Stir and crystallize with 100ml of petroleum ether to obtain 1.6g of white solid (40.0% yield), mp90°C. [α] D 20 =+29.4 (c=1, methanol)

Embodiment 2

[0034] Add 4.0g (17.9mmol) of 2-hydroxymethyl-3-(3,4-methylenedioxy)phenylpropionic acid and 5.2g (17.9mmol) of octylglucamine into a 250ml single-necked bottle, add 120ml of ethanol, After reflux for 10 minutes, it was naturally cooled to room temperature, allowed to stand for 2 days, and 3.6 g of solid was obtained by filtration. Then 100ml of ethanol was used to recrystallize 4 times to obtain 3.3g of solid.

[0035] Add 50ml of water to the solid, adjust the pH to 9 with 10% NaOH aqueous solution while stirring, filter, adjust the pH to 2 with 10% dilute hydrochloric acid in the filtrate, extract with 80ml ethyl acetate, dry over anhydrous sodium sulfate, and concentrate. Stir and crystallize with 100ml of petroleum ether to obtain 1.4g of white solid (yield 35.2%)

Embodiment 3

[0037] Add 4.0g (17.9mmol) of 2-hydroxymethyl-3-(3,4-methylenedioxy)phenylpropionic acid and 2.16g (17.9mmol) of (+)-α-phenylethylamine into a 100ml single-necked bottle 50ml of ethanol was added, refluxed for 10 minutes, cooled to room temperature naturally, left standing for 2d, and filtered to obtain 3.67g of solid. Then recrystallized twice with 30ml of ethanol to obtain 3.2g of solid.

[0038] Add 50ml of water to the solid, adjust the pH to 2 with 10% dilute hydrochloric acid under stirring, filter, and dry in vacuo to obtain 1.35g of white solid (yield 33.8%)

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Abstract

The present invention provides optically active compound 2-methylol-3-(3, 4- methylene dioxy) phenyl propionic acid and the resolution process for preparing the compound. By using substituted benzyl diethyl malonate as initial material and through basic hydrolysis, reduction and acidification, 2-methylol-3-substituted phenyl propionic acid is prepared, which is further resolved to obtain its optical isomer. The present invention has cheap material and other reagent, less wastes produced, simple operation, high yield and low cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to optical isomers obtained by resolving 2-hydroxymethyl-3-(3,4-methylenedioxy)phenylpropionic acid and a corresponding resolution method. Background technique [0002] Fasidotril (fasidotril,) is the oral prodrug of altrioprilat, developed by Bioprojet Company, licensed to Lilly Company in 2001, for the treatment of hypertension and congestive heart failure, its structure is shown in the following formula (2): [0003] [0004] Facidotril is a vasopeptidase inhibitor (Vasopeptidase inhibitor, VPI), which can simultaneously inhibit the activities of angiotensin-converting enzyme (ACE) and neutral endopeptidase (neutral endopeptidase, NEP). NEP dual inhibitors have a stronger effect on cardiac hemodynamics and kidneys than the simultaneous application of NEP inhibitors and ACE inhibitors, and are superior to any current antihypertensive drugs in terms of blood pressure reduction; in the t...

Claims

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Application Information

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IPC IPC(8): C07D317/60
Inventor 侯建赵惠清王国平何康永陈旭东
Owner SHANGHAI SHYNDEC PHARMA CO LTD
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