Efficient synthesis of 5-amino-6-dialkylamino-4-hydroxypentanamide derivatives for renin inhibitors

Heterocycles

Volumn 83, Issue 7, 2011, Pages 1587-1602

  Nakamura, Yuji ^a   Ogawa, Yasuyuki ^a   Suzuki, Chie ^a   Fujimoto, Teppei ^a   Miyazaki, Shojiro ^a   Tamaki, Kazuhiko ^a   Nishi, Takahide ^a   Suemune, Hiroshi ^b  

^a DAIICHI SANKYO CO   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79959688992     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-12224     Document Type: Article

References (15)

1. (a) G. A. MacGregor, N. D. Markandu, J. E. Roulston, J. C. Jones, and J. J. Morton, Nature, 1981, 291, 329;
2. (b) J. M. Wood, J. L. Stanton, and K. G. Hofbauer, J. Enzyme Inhib., 1987, 1, 169.
3. M. Azizi, R. Webb, J. Nussberger, and N. K. Hollenberg, J. Hypertens., 2006, 24, 243.
4. J. Maibaum, S. Stutz, R. Göschke, P. Rigollier, Y. Yamaguchi, F. Cumin, J. Rahuel, H.-P. Baum, N.-C. Cohen, C. R. Schnell, W. Fuhrer, M. G. Gruetter, W. Schilling, and J. M. Wood, J. Med. Chem., 2007, 50, 4832.
5. S. Miyazaki, Y. Nakamura, T. Nagayama, and T. Tokui, PTC Int. Appl. WO2007/148775(A1).
6. Y. Yamaguchi, K. Menear, N.-C. Cohen, R. Mah, F. Cumin, C. Schnell, J. M. Wood, and J. Maibaum, Bioorg. Med. Chem. Lett., 2009, 19, 4863.
7. R. E. Ireland, R. H. Mueller, and A. K. Willard, J. Am. Chem. Soc., 1976, 98, 2868.
8. (a) A. V. R. Rao, E. R. Reddy, B. V. Joshi, and J. S. Yadav, Tetrahedron Lett., 1987, 28, 6497;
9. (b) A. K. Ghosh, S. Leshchenko, and M. Noetzel, J. Org. Chem., 2004, 69, 7822.
10. P. Herold, R. Duthaler, G. Rihs, and C. Angst, J. Org. Chem., 1989, 54, 1178.
11. Y. Tu, Z.-X. Wang, and Y. Shi, J. Am. Chem. Soc., 1996, 118, 9806.
12. Novartis' group reported nearly the same substitution reaction.5 In the reaction, olefin 13 was reported as being produced as a major product (60% yield) together with the desired azide 12 (30% yield).
13. T. Fukuyama, C-K. Jow, and M. Cheung, Tetrahedron Lett., 1995, 36, 6373.
14. R. Göschke, S. Stutz, W. Heinzelmann, and J. Maibaum, Helv. Chim. Acta, 2003, 86, 2848.
15. H. T. Openshaw, and N. Whittaker, J. Chem. Soc. C., 1969, 89.