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The synthesis of 13 C‐enriched α‐methyldopa
Author(s) -
Ames Matthew M.,
Castagnoli Neal
Publication year - 1974
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.2590100203
Subject(s) - hydantoin , chemistry , hydrochloride , benzaldehyde , hydrolysis , hydrochloric acid , medicinal chemistry , benzoic acid , yield (engineering) , derivative (finance) , biotransformation , organic chemistry , nuclear chemistry , catalysis , materials science , economics , financial economics , metallurgy , enzyme
Alpha‐methyldopa hydrochloride, specifically labelled with 13 C in the benzylic position, was prepared for use in biotransformation studies. Carbonation of the lithio derivative of 3,4‐dibenzyloxybenzene with 13 CO 2 (64 atom percent) was followed by LiA1H 4 reduction of the resulting benzoic acid. Oxidation with CrO 3 provided the benzaldehyde which was condensed with nitroethane to form the phenylnitropropene, Reduction of this phenylnitropropene with Fe/HOAc gave the corresponding phenyl‐2‐propanone which was converted to its hydantoin derivative. Base hydrolysis of the hydantoin followed by debenzylation in concentrated hydrochloric acid gave the desired alpha‐methyldopa hydrochloride in 16% overall yield.