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Synthesis of 14C‐labelled heterocyclic analogues of phenylalanine with pyrazole and furan rings
Author(s) -
Tolman V.,
Hanuš J.,
Vereš K.
Publication year - 1968
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.2590040307
Subject(s) - hydantoin , furfural , furan , chemistry , pyrazole , alanine , hydrolysis , phenylalanine , alkylation , stereochemistry , organic chemistry , amino acid , catalysis , biochemistry
Diethyl acetamidomalonate‐2‐ 14 C was alkylated by l‐chloromethylpyrazole and the reaction intermediate hydrolyzed to give DL‐3‐(1′‐pyrazolyl)‐alanine‐2‐ 14 C. By the same method, but using 3‐chloromethylpyrazole instead of the 1‐isomer, DL‐3‐(3′‐pyrazolyl)‐alanine‐2‐ 14 C was prepared. Condensation of furfural with hydantoin‐5‐ 14 C gave 5‐(2′‐furylidene)‐hydantoin‐5‐ 14 C, which was subsequently reduced to 5‐(2′‐furyl)‐hydantoin‐5‐ 14 C and this compound was hydrolyzed to DL‐3‐(2′‐furyl)‐alanine‐2‐ 14 C. Methods for isolation and purification of the final products on microscale are described.