An improved large scale procedure for the preparation of N-Cbz amino acids

Tetrahedron Letters

Volumn 52, Issue 13, 2011, Pages 1493-1494

  Pehere, Ashok D ^a   Abell, Andrew D ^a  

^a UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

Large scale; N Cbz amino acids; Synthesis; Zofenopril

Indexed keywords

AMINO ACID; BICARBONATE; FORMIC ACID DERIVATIVE; SODIUM CARBONATE; ZOFENOPRIL;

ACYLATION; AMINO ACID SYNTHESIS; AQUEOUS SOLUTION; ARTICLE; PH;

EID: 79951950789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.102     Document Type: Article

References (17)

1. A. Isidro-Llobet, M. Alvarez, and F. Fernando Albericio Chem. Rev. 109 2009 2455
2. M. Bodanszky, and A. Bodanszky The Practice of Peptide Synthesis 1994 Springer Berlin p 11
3. J.N. Hernandez, and V.S. Martin J. Org. Chem. 69 2004 3590 3592
4. V. Pavan Kumar, M. Narender, M. Somi Reddy, K. Surendra, Y.V.D. Nageswar, and K. Rama Rao Tetrahedron Lett. 47 2006 6393 6396
5. D.B. Berkowitz, and M.L. Pedersen J. Org. Chem. 59 1994 5476 5478
6. P.E. Maligres, I. Houpis, K. Rossen, A. Molina, J. Sager, V. Upadhyay, K.M. Wells, R.A. Reamer, J.E. Lynch, D. Askin, R.P. Volante, and P.J. Reider Tetrahedron 32 1997 10983 10992
7. A.D. Abell, M.A. Jones, J.M. Coxon, J.D. Morton, S.G. Aitken, S.B. McNabb, H. Y.-Y. Lee, J.M. Mehrtens, N.A. Alexander, B.G. Stuart, A.T. Neffe, and R. Bickerstaffe Angew. Chem., Int. Ed. 48 2009 1455 1458
8. A.D. Abell, and M.D. Oldham J. Org. Chem. 62 1997 1509 1513
9. A.D. Abell, and J.M. Taylor J. Org. Chem. 58 1993 14 15
10. M.K. Edmonds, and A.D. Abell J. Org. Chem. 66 2001 3747 3752
11. A.D. Abell, and J. Gardiner Org. Lett. 4 2002 3663 3666
12. J. Krapcho, C. Turk, D.W. Cushman, J.R. Powell, J.M. DeForrest, E.R. Spitzmiller, D.S. Karanewsky, M. Duggan, G. Rovnvak, J. Schwartz, S. Natarajan, J.D. Godfrey, D.E. Ryono, R. Neubeck, K.S. Atwa, and E.W.J. Petrillo J. Med. Chem. 31 1988 1148 1160
13. 2O (100 ml) and then concentrated in vacuo to give the N-Cbz amino acid as a white solid, see Table 1.
14. P.H. Kiviranta, H.S. Salo, J. Leppanen, V.M. Rinne, S. Kyrylenko, E. Kuusisto, T. Suuronen, A. Salminen, A. Poso, M. Lahtela-Kakkonen, and E.A. Wallen Bioorg. Med. Chem. 16 2008 8054
15. Y. Shirasaki, M. Nakamura, M. Yamaguchi, H. Miyashita, O. Sakai, and J. Inoue J. Med. Chem. 49 2006 3926 3932
16. European Pharmacopoeia, 5th ed., 2005, p 434.
17. Work performed by our collaborator, Dr. Vinayak Gore of Mylan India (formally known as the Merck Development Center).