28885-22-5Relevant articles and documents
2-DIETHYLAMINOETHYL ESTERS OF 1,3-DISUBSTITUTED PROPANE-2-CARBOXYLIC ACIDS
Valenta, Vladimir,Holubek, Jiri,Svatek, Emil,Miller, Vladimir,Vlkova, Marie,Protiva, Miroslav
, p. 2534 - 2544 (2007/10/02)
Alkaline hydrolysis of diethyl 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate (IV) gave the crude acid V which was purified via the dipotassium salt and was obtained as the homogenous higher melting crystal form.Its thermic decarboxylation yielded the acid II as a mixture of two racemates (38:62); crystallization led to almost homogenous racemate B (10:90).Reaction of the sodium salt of II with dimethyl sulfate in methanol gave the methyl ester III which afforded by ester exchange with 2-diethylaminoethanol the ester I (mixture of two racemates 34:66). 2-Diethylaminoethyl 1,3-bis(1-naphthyl)propane-2-carboxylate (VII) was synthetized in three steps from diethyl (1-naphthylmethyl)malonate.Ester X was obtained from 1,3-bis(tetrahydro-2-furyl)propane-2-carboxylic acid by treatment with 2-diethylaminoethyl chloride in boiling 2-propanol in the presence of potassium carbonate.The acid V gave similarly the diester VI. 2-Diethylaminoethyl esters I, VI, VII, and X were transformed to the hydrogen oxalates.Pharmacological screening showed for the diester VI hypotensive, spasmolytic, antiarrhythmic, and antitussic activity.
