Synthesis of 14C-labeled 3-{[1-ethoxycarbonyl-3-phenyl-(1S)-phenyl-(1S)-propyl]amino}-2,3,4,5-tetrahydro-2-oxo-1H-1-(3S)-benzazepine-1-acetic acid hydrochloride ([14C]CGS 14824A)

✍ Scribed by Naba K. Chaudhuri; Russell Patera; Bohdan Markus; Ming-Sang Sung

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: French
• Weight: 334 KB
• Volume: 24
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580241005

✦ Synopsis

The title compound, CGS 148248, was synthesized with a '%-label in the azepine ring in 14 steps starting with l-bromo-3-phenylpropane (1> and K1%N in an overall yield of 1.31%. The reaction of I with K 1 k N yielded the nitrile 2 which upon hydrolysis followed by ring closure gave a-tetral~ne-l-~~c (4). Bromination of 3 followed by oxime formation gave the bromo oxime 2, which upon Beckmann rearrangement by acid treatment yielded the ring expansion product 5.

by an azido group, and an acetic ester side chain was introduced at the nitrogen atom. Catalytic reduction of the azido compound 8 gave a mixture of epimeric amino esters which was resolved by salt formation with L-tartaric acid. isomer was then reacted with 4-phenyl-2-oxo-butanoate in presence of sodium cyanoborohydride to give a mixture of diastereoisomers which were separated as their benzyl esters by chromatography. The major isomer was then converted to labeled CGS 14824A.