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Synthesis 2009(12): 1983-1986  
DOI: 10.1055/s-0029-1216813
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Substituted Benzazepin-2-one Dihydrate

Sathish K. Boini*, Radhe K. Vaid, Kenneth P. Moder, David Mitchell
Chemical Product Research and Development, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, IN 46285, USA
Fax: +1(317)2764507; e-Mail: s.boini@lilly.com;
Further Information

Publication History

Received 26 November 2008
Publication Date:
14 May 2009 (online)

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Abstract

Synthesis of the title compound was accomplished via coupling of (S)-alaninyl-(S)-1-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one with the activated trimethylsilyl ester of (S)-2-trimethylsilyloxy-3-methylbutyric acid, followed by deprotection and crystallization in situ. The starting material was prepared by the condensation of (S)-1-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one with activated N-(2-methoxycarbonyl-1-methylvinyl)-(S)-alanine sodium salt in the form of the mixed carboxylic carbonic anhydride, followed by enamine hydrolysis using methanesulfonic acid.

Key words

trimethylsilyl - (S)-2-hydroxy-3-methylbutyric acid - mixed anhydride - Dane salt

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