College of Biological and Environmental Engineering，Zhejiang Shuren University，Hangzhou 310015，China
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History+
Received
Published
2006-12-19
2007-06-10
Issue Date
2007-06-10
Abstract
OBJECTIVE To study the new synthesis of nateglinide.METHODS β-Pinene was oxidated with KMnO4 in the presence of pyridine to yield nopinic acid,then acid-catalyzed ring opened to yield dihydrocumic acid,which was hydrogenated with Pd/C and epimerizated to yield trans-4-isopropylhexanecarboxylic acid.Trans-4-isopropylhexanecarboxylic acid was changed to its acryl chloride with PCl5,reacted with D-phenylalanine to yield the title compound nateglinide.RESULTS The structures of nateglinide and trans-4-isopropylhexane carboxylic acid were identified by IR,NMR and MS.CONCLUSION This method uses the natural product β-pinene as the material,and the reaction conditions are facile and simple in all steps.
JIN Jin-zhong.
Study on Synthesis of Nateglinide [J]. Chinese Pharmaceutical Journal, 2007, 42(12): 946-948
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