147032-82-4Relevant academic research and scientific papers
Degradation Studies under Neutral and Basic Conditions on Ciprofibrate, an Orally Active Hypolipidemic Agent Containing a (4-Alkoxyaryl)-1,1-dichlorocyclopropane Unit
Dulayymi, Juma'a R. Al,Baird, Mark S.,Byard, Stephen J.,Carr, Glynis,Ellames, George J.,et al.
, p. 43 - 48 (2007/10/02)
The major product of degradation of ciprofibrate (1), 2-(4-(2,2-dichlorocyclopropyl)phenoxy>-2-methylpropanoic acid, in aqueous sodium hydroxide under reflux is 2--2-methylpropanoic acid (11).A further product, 2-(4-ethynylphenoxy)-2-methylpropanoic acid (12) is derived from 11 under the reaction conditions.A third degradant is identified as 2--2-methylpropanoic acid (13).Under similar conditions, but at pH 7, the products of degradation were found to be2--2-methylpropanoic acid (9) and (Z)-2--2-methylpropanoic acid (10).Treatment of 10 with aqueous sodium hydroxide under reflux afforded a mixture of products in which 11 and 12 predominated, whereas similar treatment of 9 led to compound 13 among other products.A labelling study indicates that the acid 21 derived from base treatment of 17 is labelled only at C-2 of the propanoic acid side chain; the same labelling pattern is observed in the acid 21 derived by base treatment of the labelled allylic alcohol 18.Mechanisms are suggested which may explain these observations.
