Details

Autor(en) / Beteiligte

• Lau, Shing-Hing
• Bourne, Samuel L
• Martin, Benjamin
• Schenkel, Berthold
• Penn, Gerhard
• Ley, Steven V

Titel

Synthesis of a Precursor to Sacubitril Using Enabling Technologies

Ist Teil von

• Organic letters, 2015-11, Vol.17 (21), p.5436-5439

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2015

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• An efficient preparation of a precursor to the neprilysin inhibitor sacubitril is described. The convergent synthesis features a diastereoselective Reformatsky-type carbethoxyallylation and a rhodium-catalyzed stereoselective hydrogenation for installation of the two key stereocenters. Moreover, by integrating machine-assisted methods with batch processes, this procedure allows a safe and rapid production of the key intermediates which are promptly transformed to the target molecule (3·HCl) over 7 steps in 54% overall yield.