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A technology of dextropropyl imine and formamide, which is applied in the field of preparation of dextropropyl imine, can solve the problems of high cost, harsh reaction conditions, and low yield
Active Publication Date: 2016-04-13
JIANGSU AOSAIKANG PHARMA CO LTD
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Problems solved by technology
The present invention aims at the problems existing in the current synthesis route of dextropropyl imine such as complex route, high cost, harsh reaction conditions, low yield and low product purity, and proposes a method with simple operation, short route, mild reaction, easy control of conditions, and low cost. Synthetic process of dextropropimine with low yield, high and stable yield, high purity of crude product and pure product
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Embodiment 1
[0078] Embodiment 1: the preparation of (S)-1,2-diaminopropane-tetraacetic acid methyl ester:
Embodiment approach 11
[0080] (S)-1,2-diaminopropane hydrochloride (500mg, 3.4mmol, 1eq), methyl bromoacetate (5202mg, 34mmol, 10eq), potassium carbonate (4692mg, 34mmol, 10eq), acetonitrile (34mL, 0.1M) were added to 100mL single-necked bottles, and reacted at 25°C for 24 hours. After the reaction was completed, the inorganic salts were filtered off, the filtrate was concentrated to dryness, and HCl (15mL, 12%) solution was added to acidify, and petroleum ether (15ml×2, 60~90℃), adjusted the pH to 10 with saturated sodium carbonate solution, extracted with dichloromethane (15ml×3), dried and concentrated to dryness to obtain the crude product (S)-1,2-diaminopropane-tetra Methyl acetate, crude product yield 55%.
Embodiment approach 12
[0082] (S)-1,2-diaminopropane hydrochloride (500mg, 3.4mmol, 1eq), methyl bromoacetate (5202mg, 34mmol, 10eq), potassium carbonate (4692mg, 34mmol, 10eq), acetonitrile (34mL, 0.1M) were added to 100mL single-necked bottles, and reacted at 25°C for 48 hours. After the reaction was completed, the inorganic salts were filtered off, the filtrate was concentrated to dryness, acidified by adding HCl (15mL, 12%) solution, and petroleum ether (15ml×2, 60~90℃), adjusted the pH to 10 with saturated sodium carbonate solution, extracted with dichloromethane (15ml×3), dried and concentrated to dryness to obtain the crude product (S)-1,2-diaminopropane-tetra Methyl acetate, crude product yield 68%.
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Abstract
The invention relates to a preparation method of dexrazoxane. In allusion to various problems of a present dexrazoxane synthetic route, such as complexity, high cost, high reaction temperature, low yield, tedious aftertreatment, long production cycle and the like, the invention provides a simple and efficient preparation method of dexrazoxane. Starting from (S)-1,2- diaminopropane hydrochloride or (S)-1,2-diaminopropane, only two steps are required to obtain a crude product dexrazoxane with the highest purity of 99.46%; and simple recrystallization is carried out to obtain a pure product with purity of 99.96%. The method has advantages of simple operation and proper temperature. By the method, the cycle of synthetic process is shortened greatly. In addition, yield and purity of the product are also raised greatly.
Description
technical field [0001] The invention belongs to the technical field of drug synthesis, specifically relates to the field of synthesis of antineoplastic drugs, and more specifically relates to a simple and efficient preparation method of dextropropimine. Background technique [0002] Dexrazoxane chemical name is (S)-(+)-4,4'-(1-methyl-1,2-ethylenediyl)-bis-2,6-piperazinedione, structure As shown in Formula-I: [0003] [0004] Dextropropylimine is the d-isomer of propyleneimine (razoxane), also known as dexrazoxane or derazoxan, and is a lipophilic derivative of the chelating agent ethylenediaminetetraacetic acid, which is used clinically for chemical protection It is mainly used to prevent anthracycline-induced cardiotoxicity. The mechanism of cardiotoxicity caused by anthracyclines is mainly due to the generation of reactive oxygen species during the formation of stable complexes between anthracyclines and iron, which cause lipid peroxidation to the myocardium and dama...
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