Practical nonazide synthesis of a D-amino acid oxidase inhibitor via a sequential erlenmeyer-plöchl reaction and ligand-free copper(I) amination protocol

Organic Process Research and Development

Volumn 18, Issue 1, 2014, Pages 198-204

  Zhao, Hang ^a,b   Koenig, Stefan G ^a,c   Dankwardt, John W ^a   Singh, Surendra P ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

^b MILLENNIUM PHARMACEUTICALS INC   (United States)

^c GENENTECH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES;

D-AMINO ACID OXIDASE; HIPPURIC ACID; INTRAMOLECULAR AMINATION; PROTECTING GROUP; REACTION MIXTURE; REGIO-SELECTIVE; RESIDUAL COPPER; SYNTHETIC ROUTES;

COPPER;

EID: 84899800545     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op4001737     Document Type: Article

References (29)

1. (a) Heffernan, M. L. R.; Fang, Q. K.; Foglesong, R. J.; Hopkins, S. C.; Ogbu, C. O.; Soukri, M.; Spear, K. L.; Orsini, M. A. PCT Int. Appl. WO 2008089453 A2 20080724, 2008.
2. (b) Sparey, T.; Abeywickrema, P.; Almond, S.; Brandon, N.; Byrne, N.; Campbell, A.; Hutson, P. H.; Jacobson, M.; Jones, B.; Munshi, S.; Pascarella, D.; Pike, A.; Prasad, G. S.; Sachs, N.; Sakatis, M.; Sardana, V.; Venkatraman, S.; Young, M. B. Bioorg. Med. Chem. Lett. 2008, 18, 3386-3391.
3. (c) Hopkins, S. C.; Heffernan, M. L. R.; Saraswat, L. D.; Bowen, C. A.; Melnick, L.; Hardy, L. W.; Orsini, M. A.; Allen, M. S.; Koch, P.; Spear, K. L.; Foglesong, R. J.; Soukri, M.; Chytil, M.; Fang, Q. K.; Jones, S. W.; Varney, M. A.; Panatier, A.; Oliet, S. H. R.; Pollegioni, L.; Piubelli, L.; Molla, G.; Nardini, M.; Large, T. H. J. Med. Chem. 2013, 56, 3710-3724.
4. Hopkins, S. C.; Zhao, F.-Y.; Bowen, C. A.; Fang, X.; Wei, H.; Heffernan, M. L. R.; Spear, K. L.; Spanswick, D. C.; Varney, M. A.; Large, T. H. J. Pharmacol. Exp. Ther. 2013, 345, 502-511.
5. Heffernan, M. L. R.; Dorsey, J. M.; Fang, Q. K.; Foglesong, R. J.; Hopkins, S. C.; Jones, M. L.; Jones, S. W.; Ogbu, C. O.; Perales, J. B.; Soukri, M. U.S. Pat. Appl. Pub. US 20080058395 A1 20080306, 2008.
6. Heffernan, M. L. R.; Dennis, R.; Dorsey, J. M.; Foglesong, R. J.; Jones, M. L.; Ogbu, C. O.; Soukri, M.; Spear, K. L.; Wilkinson, S. H.; Orsini, M. A. PCT Int. Appl. WO 2010017418 A1 20100211, 2010.
7. (a) Hemetsberger, H.; Knittel, D. Monatsh. Chem. 1972, 103, 194-204.
8. (b) Welch, M.; Phillips, R. S. Heterocycl. Commun. 1999, 5, 305-310.
9. (c) Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500-7501.
10. (a) Boyer, J. H.; Moriarty, R.; Darwent, B. de B.; Smith, P. A. S. Chem. Eng. News 1964, 42, 6.
11. (b) Hagenbuch, J.-P. Chimia 2003, 57, 773-776.
12. For a discussion of process safety considerations or working with azides in batch equipment, see: Kopach, M. E.; Murray, M. M.; Braden, T. M.; Kobierski, M. E.; Williams, O. L. Org. Process Res. Dev. 2009, 13, 152-160.
13. A continuous flow approach was subsequently demonstrated to form the methyl ester of 5; however, this paper did not address handling the azido acrylate precursor or the use of sodium azide: O'Brien, A. G.; Lévesque, F.; Seeberger, P. H. Chem. Commun. 2011, 47, 2688-2690 and the references cited therein.
14. (a) Barberis, C.; Gordon, T. D.; Thomas, C.; Zhang, X.; Cusack, K. P. Tetrahedron Lett. 2005, 46, 8877-8880.
15. (b) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428-2439.
16. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
17. (d) Evano, G.; Toumi, M.; Coste, A. Chem. Commun. 2009, 4166.
18. (e) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469-6480 and references therein.
19. Zhao, H.; Dankwardt, J. W.; Koenig, S. G.; Singh, S. P. Tetrahedron Lett. 2012, 53, 166-169.
20. Xu, F.; Devine, P. Org. Process Res. Dev. 2010, 14, 666-667.
21. (a) Erlenmeyer, E. Liebigs Ann. Chem. 1893, 275, 1-8.
22. (b) Plöchl, J. Chem. Ber. 1884, 17, 1616-1624.
23. (a) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120-4121.
24. (b) Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13-31.
25. (c) Sperotto, E.; van Klink, G. P. M.; van Koten, G.; de Vries, J. G. Dalton Trans. 2010, 39, 10338-10351.
26. For a related, ligand-free method, see: Melkonyan, F. S.; Karchava, A. V.; Yurovskaya, M. A. J. Org. Chem. 2008, 73, 4275-4278. Also, see refs 9b and 16 for other ligandless results.
27. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
28. (a) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231-234.
29. (b) Koenig, S. G.; Dankwardt, J. W.; Liu, Y.; Zhao, H.; Singh, S. P. Tetrahedron Lett. 2010, 51, 6549-6551.