A kind of synthetic method of optically active intermediate n-tert-butoxycarbonyl-2-amino-8-nonenoic acid dicyclohexylamine salt

Abstract

The invention discloses a method for synthesizing an optically active intermediate N-tert-butoxycarbonyl-2-amino-8-nonenoic dicyclohexylamine salt. The method includes: taking acetamino malonate as an original raw material, performing alkylation reaction, hydrolysis and decarboxylation to generate an intermediate IV, subjecting the intermediate IV to tert-butoxycarbonyl protection to obtain an intermediate III, hydrolyzing the intermediate III under the action of enzymes to obtain an intermediate II, and allowing salt forming reaction between the intermediate II and dicyclohexylamine to obtain the target product. The method has the advantages of short synthetic route, easiness in purification of the synthesized product, mild reaction conditions and environment friendliness; the required raw material is cheap and low in cost; the obtained product is high in yield and quality and suitable for mass industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for synthesizing an optically active intermediate N-tert-butoxycarbonyl-2-amino-8-nonenoic acid dicyclohexylamine salt. Background technique [0002] Viral hepatitis C, referred to as hepatitis C, hepatitis C, is a viral hepatitis caused by hepatitis C virus (HCV) infection, mainly through blood transfusion, acupuncture, drug abuse, etc., according to the statistics of the World Health Organization, the global The infection rate of HCV is about 3%, it is estimated that about 180 million people are infected with HCV, and there are about 35,000 new cases of hepatitis C every year. Hepatitis C is a global epidemic, which can lead to chronic inflammation, necrosis and fibrosis of the liver, and some patients can develop liver cirrhosis or even hepatocellular carcinoma. The mortality rate associated with HCV infection will continue to increase in the next 20 yea...

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Problems solved by technology

[0014] 4. Azidation: The reaction uses strong bases such as butyl lithium and KHDMS, which have relatively high requirements on the operating environment (strictly anhydrous, ultra-low temperature, etc.), and are not suitable for scale-up production

[0020] (1) The route for synthesizing N-tert-butoxycarbonyl-2-amino-8-nonenoic acid dicyclohexylamine salt is long, the purification is cumbersome, and the conditions of the synthesis process are harsh;

[0021] (2) The required raw materials for the synthesis of N-tert-butoxycarbonyl-2-amino-8-nonenoic acid dicyclohexylamine salt are expensive and the cost is high;

[0022] (3) the yield of gained product is low, is unfavorable for industrialized large-scale production

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