Synthesis of Derivatives of Acylaminoadamantane Carboxylic Acids and some Transformations

摘要

Amethodology for synthesis of 3-acetylamino-, 3-acetylaminophenyl- and 3-hydroxyadamantane-1-carboxylic acids. Certain amino acids are synthesized by acid hydrolysis of acyl derivatives. A supposed mechanism of the reaction 3-acetaminoadamantane-l-carboxylic acid is given. Found, that high-purity 3-acetylaminoadamantane-l-carboxylic acid is obtained by interaction of 3-hydroxyadamantane-l-carboxylic acid and acetonitriie in the sulfuric acid medium.Two products are obtained as a result of hydrolysis of 3-acetyIaminoadamantane-l-carboxylic acid in aqueous solution of HCL boiling for 5-10 hrs. Those are main product 3-aminoadamantane-l-carboxylic acid hydrochloride and by-product 3-chloradamantane-l-carboxylic acid. Be nzoylation of 3-aminoadamantane-l-carboxylic acid hydrochloride is conducted and 3-(N-benzoyl)aminoadamantane-l-carboxylic acid is obtained. Structure of synthesized compounds is confirmed by the data of IR, H-NMR, C-NMRspectra.