A convenient and new approach to the synthesis of ω-heterocyclic amino acids from carboxy lactams through ring-chain-transformation. Part 2: Synthesis of (2R)-/(2S)-2-aminomethyl-3-(1-aryl-/1,5-diaryl-1H-pyrazol-3-yl)- propionic acid

Tetrahedron

Volumn 61, Issue 37, 2005, Pages 8868-8874

  Singh, Rakesh K ^a,c   Sinha, Neelima ^a,d   Jain, Sanjay ^a,d   Salman, Mohammad ^a   Naqvi, Fehmida ^b   Anand, Nitya ^a  

^a Ranbaxy Laboratories Limited   (India)

^b JAMIA MILLIA ISLAMIA CENTRAL UNIVERSITY   (India)

^c BROWN UNIVERSITY   (United States)

^d LUPIN LIMITED   (India)

Author keywords

2 Aminomethyl 3 (substituted 1H pyrazol 3 yl) propionic acid; Chirality; Hydrogenation; Ring chain transformation reaction; Sulfur extrusion reaction; Unnatural amino acids

Indexed keywords

2 AMINOMETHYL 3 (1H PYRAZOL 3 YL)PROPIONIC ACID; AMIDE; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; ISOMERISM; MASS SPECTROMETRY; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 23644443626     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.018     Document Type: Article

References (25)

1. R.O. Duthaler Tetrahedron 50 1994 1539
2. R.M. Williams Aldrichim. Acta 25 1992 11
3. Y. Izumi, I. Chibata, and T. Itoh Angew. Chem., Int. Ed. Engl. 17 1978 176
4. J. Brunner Chem. Soc. Rev. 22 1993 183
5. M. Chorev, and M. Goodman Acc. Chem. Res. 26 1993 266
6. R.J. Bridges, J.W. Geddes, D.T. Monaghan, and C.W. Cotman D. Lodge Excitatory Amino Acids in Health and Diseases 1988 Wiley New York 321
7. S. Patel, A.G. Chapman, M.H. Millan, and B.S. Meldrum D. Lodge Excitatory Amino Acids in Health and Diseases 1988 Wiley New York 353
8. G.K. Stienberg, J. Saleh, D. Kunis, R. DeLaPaz, and S.R. Zarnegar Stroke 20 1989 1247
9. T.N. Johansen, K. Frydenvang, B. Ebert, P. Krogsgaard-Larsen, and U. Madsen J. Med. Chem. 37 1994 3252 and references cited therein
10. V.J. Hruby, F. al-Obeide, and W. Kazmierski Biochem. J. 268 1990 249 and references cited therein
11. D.H. Apella, L.A. Christianson, D.A. Klein, D.R. Powell, X. Huang, J.J. Barchi Jr., and S.H. Gellman Nature 387 1997 381
12. K. Gademann, T. Hintermann, and J.V. Schreiber Curr. Med. Chem. 6 1999 905
13. W.F. DeGrado, J.P. Schneider, and Y. Hamuro J. Pept. Res. 54 1999 206
14. K.A. Bode, and J. Applequist Macromolecules 30 1997 2144
15. D. Seebach, and J.L. Matthews Chem. Commun. 1997 2015
16. B.L. Iverson Nature 385 1997 113
17. D. Seebach, M. Overhand, F.N.M. Kuhnle, B. Martinoni, L. Oberer, U. Hommel, and H. Widmer Helv. Chim. Acta 9 1996 913
18. S. James Chim. Oggi/Chem. Today 2003 65
19. Singh, R. K.; Sinha, N.; Jain, S.; Salman, M.; Naqvi, F.; Anand, N. Synthesis, in press.
20. Sysko, R. J.; Tate, B. E. Eur. Pat. Appl. EP69512, 1983; Chem. Abstr. 1983, 98, 166765.
21. V. Virmani, M.B. Nigam, P.C. Jain, and N. Anand Indian J. Chem. 17B 1979 472
22. J. Singh, V. Sardana, P.C. Jain, and N. Anand Indian J. Chem. 22B 1983 1083
23. M. Pätzel, and J. Liebscher Synthesis 1995 879
24. T.P. Culbertson, J.M. Domagala, J.B. Nichols, S. Priebe, and R.W. Skeean J. Med. Chem. 30 1987 1711
25. L. Nielsen, L. Brehm, and P. Krogsgaard-Larsen J. Med. Chem. 33 1990 71