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Synthesis of N-[N-[(S)-1-ethoxy[14C]carbonyl-3-phenyl[1-14C]propyl]-L-alanyl]-N-(indan-2-YL)glycine hydrochloride ([14C]CV-3317)

✍ Scribed by Masazumi Watanabe; Norio Tada; Katsumi Itoh; Nobuyoshi Hayashi

Publisher
John Wiley and Sons
Year
1987
Tongue
French
Weight
176 KB
Volume
24
Category
Article
ISSN
0022-2135

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✦ Synopsis

N-[N-[(S)-1-Ethoxycarbonyl

-3-phenylpropyll-La l a ~y l ~-E -T i n d a n -2 -y 1 ) glycine hydrochloride (CV-3317) , a new potent angiotensin converting enz e inhibitor, was labeled with carbon-14. Diethyl [U-'C]oxalate was condensed with ethyl 3-phenylpropionate, subsequently decarboxylated to yield ethyl [1,2-14C]-2-oxo-4-phenylbutyrate. The reductive condensation of the latter with tert-butyl E-L-alanyl-N-('ndan-2-yl)glycinate followed b y y d r o l y s i s afforded [15 CICV-3317 in an overall radiochemical yield of 17.4 %.

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