129939-63-5Relevant articles and documents
A PROCESS FOR THE PREPARATION OF 2-[N-- [(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-(S)-ALANYL]-(1S, 3S, 5S) -2-AZABICYCLO [3.3.0] OCTANE-3--CARBOXYLIC ACID
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Page/Page column 12, (2008/06/13)
A process for preparation of 2-[N-[(S)-l--ethoxycarbonyl-3-phenylpropyl] - (S) -alanyl]-(1S, 3S, 5S)-2-- azabicyclo [3.3.0 ] octane-3-carboxylic acid, ie. Ramipril, involves condensation of an activated derivative of 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine with racemic (1R*, 3R*, 5R*) -2-azabicyclo [3.3.0] octane-3--carboxylic acid, and then the desired diastereoisomer (la) is separated from the obtained diastereoisomeric mixture of 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-(S) -alanyl] - (1S, 3S, 5S) -2-azabicyclo [3.3.0] octane-3--carboxylic acid (1a) and 2- [N-[(S)-1-ethoxycarbonyl-3--phenylpropyl ] - (S) -alanyl ] - (1R, 3R, 5R) -2- azabicyclo[3.3.0]octane-3-carboxyl ic acid (lb) by treat-ing it with a solvent that selectively dissolves the un-desired diastereoisomer (1b) while the diastereoisomer (1a) remains undissolved.