Greening the Valsartan Synthesis: Scale-up of Key Suzuki-Miyaura Coupling over Silia Cat DPP-Pd

Organic Process Research and Development

Volumn 17, Issue 12, 2013, Pages 1492-1497

  Pandarus, Valerica ^a   Desplantier Giscard, Delphine ^a   Gingras, Geneviève ^c   Béland, François ^a   Ciriminna, Rosaria ^b   Pagliaro, Mario ^b  

^a SiliCycle Inc   (Canada)

^b CNR   (Italy)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

CONTINUOUS COUPLINGS; COUPLING PRODUCT; HIGH YIELD SYNTHESIS; OPTIMAL REACTION CONDITION; SCALE-UP; SUZUKI-MIYAURA COUPLING; SUZUKI-MIYAURA COUPLING REACTION; VALSARTAN;

CHEMISTRY;

SYNTHESIS (CHEMICAL);

EID: 84890848292     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op400118f     Document Type: Article

References (14)

1. Wexler, R. R.; Greenlee, W. J.; Irvin, J. D.; Goldberg, M. R.; Prendergast, K.; Smith, R. D.; Timmermans, P. B. M. W. M. J. Med. Chem. 1996, 39, 625-656
2. Kearney, P. M.; Whelton, M.; Reynolds, K.; Muntner, P.; Whelton, P. K.; He, J. Lancet 2005, 365, 217-223
3. Longstreet, A. R.; McQuade, D. T. Acc. Chem. Res. 2012, 46, 327-338
4. McQuade, D. T. A Flow Chemistry Approach To Catalysis. FineCat 2013-Symposium on heterogeneous catalysis for fine chemicals, Palermo, Italy, 10-11 April 2013.
5. Bühlmayer, P.; Furet, P.; Criscione, L.; de Gasparo, M.; Whitebread, S.; Schmidlin, T.; Lattmann, R.; Wood, J. Bioorg. Med. Chem. Lett. 1994, 4, 29-34
6. Goossen, L. J.; Melzer, B. J. Org. Chem. 2007, 72, 7473-7476
7. Beutler, U.; Boehm, M.; Fuenfschilling, P. C.; Heinz, T.; Mutz, J.-P.; Onken, U.; Mueller, M.; Zaugg, W. Org. Process Res. Dev. 2007, 11, 892-898
8. Ghosh, S.; Kumar, A. S.; Mehta, G. N. Beilstein J. Org. Chem. 2010, 6, No. 27
9. As stated by Dunn, the range of 25-100 kg of waste per kilogram of API proposed by Sheldon in 1992 at the end of the "racemic era" is probably now more realistically 25-200 in the "chiral era: Dunn, P. J. Chem. Soc. Rev. 2012, 41, 1452-1461
10. EPA Office of the Inspector General. EPA Inaction in IdentifyingHazardous Waste Pharmaceuticals May Result in Unsafe Disposal, ReportNo. 12-P-0508; Washington, May 25, 2012.
11. Lemay, M.; Pandarus, V.; Simard, M.; Marion, O.; Tremblay, L.; Béland, F. Top. Catal. 2010, 53, 1059-1062
12. Pandarus, V.; Gingras, G.; Béland, F.; Ciriminna, R.; Pagliaro, M. Org. Process Res. Dev. 2012, 16, 117-122
13. Molander, G. A.; Trice, S. L. J.; Dreher, S. D. J. Am. Chem. Soc. 2010, 132, 17701-17703
14. Pandarus, V.; Ciriminna, R.; Gingras, G.; Béland, F.; Drobod, M.; Jina, O.; Pagliaro, M. Tetrahedron Lett. 2013, 54, 1129-1132