Synthesis of a Substituted Benzazepin-2-one Dihydrate

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

References

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