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A kind of enalapril intermediate synthetic mother liquor prepares the method for 3-benzoyl ethyl acrylate
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A technology for synthesizing ethyl benzoyl acrylate and mother liquor, which is applied in the fields of preparing 3-benzoyl ethyl acrylate from enalapril intermediate synthesis mother liquor and preparing compounds from mother liquor of pharmaceutical and chemical intermediates, which can solve the problem that the product is not separated, There are many impurities in the reaction process, narrow application range and other problems, so as to achieve the effects of low cost, convenient operation and improved utilization rate
Active Publication Date: 2020-11-06
ZHEJIANG UNIV OF TECH +1
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[0006] In 1967, Ronald's research group first synthesized amine compounds to form sulfonates, and then heated them in sodium hydroxide solution to remove amino groups. The yield of this process was between 29% and 51%. Toluenesulfonic acid, p-toluenesulfonic acid, sulfonylimide anion, etc., this type of reaction is more suitable for the deamination reaction of primary amines, but there are many impurities in the reaction process (TheJournal of Organic Chemistry, 1968, 30 (1); 234-237.)
[0007] In 2013, Zhejiang Huahai Pharmaceutical Co., Ltd. proposed to heat amino acid compounds under acidic conditions. Finally, all the raw materials were hydrolyzed, and the reaction was carried out in acidic medium. The reaction conditions were simple, but the reaction time was long, and the products in the reaction solution were not separated. Come out, the reaction has a good reference value (CN103360259A)
[0009] Summarizing the deamination elimination methods reported so far, there are mainly the following problems: (1) Alkaline catalysts are currently commonly used methods, but this method is not suitable for easily hydrolyzed compounds containing ester groups (2) Using acids as catalysts is suitable for Narrow range, more impurities in the reaction
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Embodiment 1
[0030] In a 2000.0 mL three-neck flask equipped with a water separator, drop 1000.0 g of the above-mentioned enalapril intermediate synthesis mother liquor (components: I 3.0%, II 6.0%, III 7.0%, ethanol 84%, water 0%, other 0% %), heated to reflux conditions to remove ethanol and water, add catalyst trifluoromethanesulfonate p-methoxyanilinium salt 12.7 g, toluene 500 mL, reflux reaction for 1 h, after the reaction, add water to wash, keep the organic layer, The organic solvent was concentrated to obtain 114.5 g of compound (I), with a yield of 95% and a purity of 97.8%.
Embodiment 2
[0032] Add 20.0 g of compound (II) (100%), 200.0 mL of dichloromethane, and 1.5 g of aniline trifluoromethanesulfonate into a four-neck flask, heat to reflux for 8 h, and directly separate the organic layer after the reaction Yes, 13.3 g of ethyl 3-benzoylacrylate was obtained, with a yield of 95.5% and a purity of 96.5%.
Embodiment 3
[0034] Into the 2000.0 mL three-necked flask equipped with a water separator, 1000.0 g of the above-mentioned enalapril intermediate synthesis mother liquor (components: I 10.0%, II 10.0%, III 2.0%, ethanol 73.2%, water 3.5%, other 1.3% %), heated to reflux conditions to remove ethanol and water, add 15.8 g of benzylamine trifluoromethanesulfonate catalyst, 500 mL of cyclohexane, reflux for 2 h, after the reaction, wash with water, keep the organic layer, and The organic solvent was concentrated to obtain 176.8 g of compound (I), with a yield of 96.3% and a purity of 98.3%.
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Abstract
The invention discloses a method of preparing ethyl 3-benzoylacrylate from enalapril intermediate synthesis mother liquor. In a device provided with a reflux water separator, ethanol and water of enalapril key intermediate synthesis mother liquor, which contains compounds represented by the formulas (I), (II), and (III), are removed under reflux conditions; then an organic solvent and a catalyst is added to carry out reactions under heating, compounds (II) and (III) carry out de-amination elimination reactions under the effect of the catalyst to generate the compound (I), after reactions, the reaction product is washed by water, the organic layer is saved, and the organic solvent is concentrated to obtain the compound (I). The preparation method has the advantages of simple technology and convenient operation. The mother liquor, which is obtained after separation and purification of the compound (II), is recovered and utilized. After the recovered ethyl 3-benzoylacrylate is processed, ethyl 3-benzoylacrylate can be used as a raw material to prepare the compound (II), the utilization rate of ethyl 3-benzoylacrylate is increased, and the method has a great value in industry.
Description
technical field [0001] The invention relates to a method for preparing a compound from a mother liquor of a pharmaceutical and chemical intermediate, and belongs to the technical field of pharmacy, in particular to a method for preparing 3-benzoyl ethyl acrylate from a mother liquor of an enalapril intermediate synthesis. Background technique [0002] Enalapril (Ramipril) is a second-generation angiotensin-converting enzyme inhibitor (ACEI) drug developed by Merck in the United States. It was first launched in West Germany in 1984 and is the drug of choice for the treatment of mild to moderate hypertension. , the drug has the characteristics of small side effects, good oral absorption, long-lasting and powerful effect and the like. [0003] Compound (II) is the key intermediate for the preparation of enalapril, which is synthesized by the Michael addition reaction of compound (I) and L-alanine. After the reaction, there will be part of compound (I) in the mother liquor , Co...
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