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Process for preparing fudosteine

A compound, addition reaction technology, applied in respiratory diseases, organic chemistry, drug combination, etc., can solve the problems of high production equipment requirements, high cost, good solubility, etc., and achieve the effect of improving product quality and reducing requirements

Active Publication Date: 2006-10-04
AVENTIS PHARMA HAINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the following disadvantages: the reaction time is too long, and bromide, strong acid, strong alkali and other substances are involved in the reaction, which will cause great damage to the equipment, and due to the existence of bromide, there are serious environmental protection problems, resulting in increased costs
This method has the following disadvantages: because the catalysts used are all salts, and the polarity of the final product fudosteine ​​is relatively large, and the solubility in aqueous solution is good, it is difficult to separate the final product and the catalyst well, thereby Lead to residual salts in the final product, resulting in poor quality
The method of synthesizing fudosteine ​​by docking L-cysteine ​​and allyl alcohol under the catalysis of strong light irradiation is not easy to realize large-scale industrial production due to high requirements on production equipment due to strong light irradiation

Method used

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  • Process for preparing fudosteine
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  • Process for preparing fudosteine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0022] Dissolve 2.0 g (16.5 mmol) of L-cysteine ​​in 20 ml of water, add 1.95 g (33 mmol) of allyl alcohol, and stir at room temperature. Add 200 mg of ferrous chloride and 200 mg of ammonium peroxodisulfate and continue stirring for 15 minutes. After the reaction, the solvent was evaporated under reduced pressure, ethanol (25%) was added to the residue, the insolubles were filtered off, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from a water-ethanol system to obtain 2.3 g of colorless crystals with a yield of 80%. %.

Embodiment 3

[0024] Dissolve 2.0 g (16.5 mmol) of L-cysteine ​​in 20 ml of water, add 1.95 g (33 mmol) of allyl alcohol, and stir at room temperature. Add 200 mg of ferrous chloride and 200 mg of ammonium peroxodisulfate, and irradiate with a low-pressure mercury lamp (250-310 nm, 10 W) for 30 minutes. After the reaction, the residue was washed with ethyl acetate, the aqueous phase was concentrated under reduced pressure, and the residue was recrystallized from a water-ethanol system to obtain 2.78 g of colorless crystals, with a yield of 80%.

[0025] Embodiment of this patent

Embodiment 1

[0027] Mix 8.5L distilled water and 1.9kg L-cysteine, there is a small amount of insoluble matter. Add 2.2L propenyl alcohol, and it becomes a white cloudy liquid. After the addition is complete, heat to 50-60°C and stir to react for more than 7 hours. Stirring was stopped, and 45 L of acetone was added dropwise to the reaction solution to precipitate a white solid. After dropping, continue to stir for 45 minutes, let stand for 0.5-1.0 hours, filter with suction to obtain a white solid, rinse the upper layer solid with 3-5L acetone. The obtained solid was dried at 45° C. for 24 hours to obtain 2.0 kg of product, with a yield of 80%.

[0028] Example 2:

[0029] Mix 4.3L distilled water and 1.0kg L-cysteine, there is a small amount of insoluble matter. Add 0.6L propenyl alcohol, and it becomes a white cloudy liquid. After the addition is complete, heat to 50-60°C and stir to react for more than 7 hours. Stirring was stopped, and 23 L of acetone was added dropwise to the r...

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Abstract

The invention provides a process for preparing Fudosteine, which has the chemical structural formula (I) disclosed in the specification. The Fudosteine can be used as the medicament for relieving cough and expectorant.

Description

field of invention [0001] The invention relates to a preparation method of fudosteine, and the compound can be used as an antitussive and phlegm-reducing medicine. Background of the invention [0002] Fudosteine ​​(chemical name: 3-hydroxypropylthioalanine), has the following structure: [0003] [0004] Fudosteine ​​can effectively reduce the secretion of mucus in patients with chronic respiratory diseases, so it has good antitussive and phlegm-reducing effects. [0005] At present, the methods for synthesizing fudosteine ​​all use L-cysteine ​​as the starting material, which is prepared by docking with different branched side chains. The published synthetic methods of fudosteine ​​are as follows: [0006] The method for preparing L-cysteine ​​and 3-bromo-1 propanol under the catalysis of a strong base is found in the document Biochemistry 1991, 30, 4078-4081, the method comprising: a) L-cysteine Add 3-bromo-1 propanol into a strong alkaline aqueous solution such as so...

Claims

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Application Information

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IPC IPC(8): C07C323/58A61P11/14A61P11/10
Inventor 曲峰李彦
Owner AVENTIS PHARMA HAINAN
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