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Synthesis of homovanillic acid‐2− 14 C, homoprotocatechuic acid‐2− 14 C, 3′, 4′‐dihydroxymandelic acid‐2− 14 C and 1‐(4 hydroxy‐3‐methoxyphenyl)‐ethylene glycol‐1− 14 C
Author(s) -
Liebman A. A.,
Malarek D. H.,
Dorsky A. M.,
Kaegi H. H.
Publication year - 1971
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590070410
Subject(s) - phenylacetic acid , chemistry , mandelic acid , benzoic acid , ethylene , homovanillic acid , organic chemistry , medicinal chemistry , catalysis , biochemistry , receptor , serotonin
Abstract Specifically labelled phenylacetic acid and mandelic acid derivatives, metabolites of L‐Dopa, have been synthesized via the intermediary labelled benzyl alcohols, which were prepared by reduction of the methyl esters of the appropriate benzoic acids. The benzyl alcohols have been converted to the corresponding phenylacetonitriles via the intermediate chlorides and to the cyanohydrins via the intermediate aldehydes in yields significantly higher than previously reported. Overall radiochemical yields of the title compounds were in the order of 25% from 14 CO 2 and specific activities ranged from 4–10 mC/mmole. The collated procedures have general applicability.