A facile synthesis of N-Fmoc protected amino/peptidyl Weinreb amides employing acid chlorides as key intermediates

Arkivoc

Volumn 2008, Issue 2, 2008, Pages 243-249

  Sureshbabu, Vommina V ^a   Hemantha, H P ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Acid chlorides; N,O dimethylhydroxylamine; N Fmoc amino acids peptide acids; Ultrasonication; Weinreb amides

Indexed keywords

EID: 42249099173     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.226     Document Type: Article

References (26)

1. (a) Sibi M. P. Org Prep Proced In. 1993, 25, 15.
2. (b) Banwell, M.; Smith, J. Synth Commun. 2001, 31, 2011.
3. Banwell, M.; Edwards, A.; Smith, J.; Hame, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. I, 2000, 1497.
4. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
5. Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
6. Dickson H. D.; Smith S. C.; Hinkle K. W. Tetrahedron Lett. 2004, 45, 5597.
7. Angelo N. G.; Arora P. S. J. Am. Chem. Soc. 2005, 127, 17134.
8. Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
9. Kim, M.; Lee, H.; Han, K. J.; Kay, K. Y. Synth Commun. 2003, 33, 4013.
10. Shreder, K.; Zhang, L.; Goodman, M.; Tetrahedron Lett. 1998, 39, 253.
11. Braun, M. Synthesis 1989, 856.
12. Raghuram, T.; Vijayasaradhi, S.; Singh, I.; Singh, J. Synth Commun. 1999, 29, 3215.
13. Katritzky, A. R.; Yang, H.; Zhang, S.; Wang, M. ARKIVOC 2002, (xi), 39.
14. Luca, L. D.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534.
15. Tunoori, A. R.; White, J. M.; Georg, G. I. Org. Lett. 2000, 2, 4091.
16. Carpino, L. A.; Cohen, B. J.; Stephens, J. K. E.; Sadat-Aalaee, S. Y.; Tien, J. H.; Langridge, D. C. J. Org. Chem. 1986, 51, 3732.
17. Carpino, L. A. J. Org. Chem. 1988, 53, 875.
18. Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C. Eds. Houben-Weyl: Synthesis of Peptides & Peptidomimetics; Georg Thieme Verlag: Stuttgart, New York, 2003; Vol. E22, pp 475-491.
19. Gopi, H. N.; Sureshbabu, V. V. Tetrahedron Lett. 1998, 39, 9769.
20. Sureshbabu, V. V.; Gayathri, K. Indian J. Chem. 1998, 37(B), 1109.
21. Gopi, H. N.; Sureshbabu, V. V. Tetrahedron Lett. 1998, 39, 1049.
22. Tantry, S. J.; Sureshbabu, V. V. Lett. Peptide Science, 2002, 9, 35.
23. Gopi, H. N.; Sureshbabu, V. V. J. Indian Chem. Soc. 1998, 75, 511.
24. Sureshbabu, V. V.; Gayathri, K.; Gopi, H. N. Synth. Commun. 1999, 29, 79.
25. Kantharaju; Patil, B. S.; Sureshbabu, V. V. Lett. Peptide Science, 2002, 9, 227.
26. Gayathri, K.; Gopi, H. N.; Sureshbabu, V. V. Indian J. Chem. 1998, 37(B), 151.