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) | Zendy

Watanabe Masazumi | Zendy; Tada Norio | Zendy; Itoh Katsumi | Zendy; Hayashi Nobuyoshi | Zendy

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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

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 %.

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