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Synthesis of N ‐[ N ‐[( S )‐1‐ethoxy[ 14 C]carbonyl‐3‐phenyl[1‐ 14 C]propyl]‐L‐alanyl]‐ N ‐(indan‐2‐YL)glycine hydrochloride ([ 14 C]CV‐3317)
Author(s) -
Watanabe Masazumi,
Tada Norio,
Itoh Katsumi,
Hayashi Nobuyoshi
Publication year - 1987
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580241204
Subject(s) - chemistry , yield (engineering) , hydrolysis , alkoxy group , medicinal chemistry , hydrochloride , stereochemistry , glycine , nuclear chemistry , alkyl , organic chemistry , amino acid , biochemistry , materials science , metallurgy
Abstract N ‐[ N ‐[( S )‐1‐Ethoxycarbonyl‐3‐phenylpropyl]‐L‐alanyl]‐ N ‐(indan‐2‐yl)glycine hydrochloride (CV‐3317), a new potent angiotensin converting enzyme inhibitor, was labeled with carbon‐14. Diethyl [U‐ 14 C]oxalate was condensed with ethyl 3‐phenylpropionate, subsequently decarboxylated to yield ethyl [1,2‐ 14 C]‐2‐oxo‐4‐phenylbutyrate. The reductive condensation of the latter with tert ‐butyl N ‐L‐alanyl‐ N ‐(indian‐2‐yl)glycinate followed by hydrolysis afforded [ 14 C]CV‐3317 in an overall radiochemical yield of 17.4 %.