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Synfacts 2012; 8(2): 0121
DOI: 10.1055/s-0031-1289963
DOI: 10.1055/s-0031-1289963
Synthesis of Natural Products and Potential Drugs
Synthesis of a Precursor to LY2140023
Waser M, * Moher ED et al.. * DSM Fine Chemicals Austria Nfg GmbH & Co KG, Linz, Austria and Eli Lilly and Company,
Indianapolis, USA
Process Development for a Key Synthetic Intermediate of LY2140023, a Clinical Candidate for the Treatment of Schizophrenia.
Org. Process Res. Dev. 2011;
15: 1266-1274
Process Development for a Key Synthetic Intermediate of LY2140023, a Clinical Candidate for the Treatment of Schizophrenia.
Org. Process Res. Dev. 2011;
15: 1266-1274
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Further Information
Publication History
Publication Date:
19 January 2012 (online)
Significance
LY2140023 is a conformationally restricted glutamic acid analogue that is an mGlu2/3 receptor agonist. It entered phase II clinical trials for the treatment of schizophrenia. The following synthesis was used to deliver over one metric ton of the key intermediate K.
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Comment
Whilst the later steps are described on large scale, the earlier steps, especially the critical carbene insertion reaction leading to cyclopropane B, is reported on a small scale. A large-scale (206 mol) hydroboration of B using BH3·THF complex is described.
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