Process for the synthesis of the ace inhibitor trandolapril

Details Process for the synthesis of the ace inhibitor trandolapril Process for the synthesis of the ace inhibitor trandolapril

C - Chemistry, Metallurgy

07

D

C07D 209/42 (2006.01)

Patent

CA 2614099

A process for the synthesis of trandolapril which comprises condensing N-[I- (S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride with trans octahydro-1H- indole-2-carboxylic acid in a first organic solvent comprising a water immiscible inert organic solvent and in the presence of a base, and isolating trandolapril from a second organic solvent. N-[1-(S)-ethoxycarbonyl- 3-phenylpropyl]-L-alanine N-carboxyanhydride may also be condensed with (2S,3aR,7aS) octahydro-1H-indole-2-carboxyIic acid in a first organic solvent and in the presence of a base, and trandolapril isolated. There is also provided a process for the resolution of racemic trans octahydro-1H-indole-2- carboxylc acid.

L'invention porte sur un procédé de synthèse de trandolapril qui consiste à condenser N-[I-(S)-éthoxycarbonyl-3-phénylpropyl]-L-alanine N-carboxyanhydride avec l'acide trans octahydro-1H-indole-2-carboxylique dans un premier solvant organique comprenant un solvant organique inerte immiscible dans l'eau et en présence d'une base, et isoler trandolapril d'un second solvant organique. N-[1-(S)-éthoxycarbonyl-3-phénylpropyl]-L-alanine N-carboxyanhydride peut être également condensé avec l'acide (2S,3aR,7aS)octahydro-1H-indole-2-carboxyIique dans un premier solvant organique et en présence d'une base, trandolapril étant ainsi isolé. L'invention porte également sur un procédé de résolution de l'acide racémique trans octahydro-1H-indole-2-carboxylique.

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