Tytuł artykułu
Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
An efficient method of synthesis of N-t-butoxycarbonyl-azaamino acid ethyl esters has been described. This method consisted of three stages including: hydrazone formation, its reduction and acylation with ethyl chloroformate. The second step - reduction of the hydrazones to the appropriate hydrazides - was the most challenging. Some reducing agents have been tested, though NaBH3CN was found to lead to the final products with the highest yields in relatively short time and even to allow the selective reduction of C-N bond in the presence of nitro group.
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
1693--1697
Opis fizyczny
Bibliogr. 14 poz., rys.
Twórcy
autor
- Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
autor
- Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
autor
- Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
autor
- Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
Bibliografia
- 1. Gante J., Synthesis, 405 (1989) and references cited therein.
- 2. Niedrich H., J. Prakt. Chem., 314, 769 (1972).
- 3. Powers J.C., Boone R, Carroll D.L., Gupton F., Kam C.-M., Nishino N., Sakamoto M. and Tuhy P.M., J. Biol. Chem., 259, 4288 (1984).
- 4. Magrath J. and Abeies R.H., J. Med. Chem., 35,4179 (1992).
- 5. Baggio R., Shi Y.-Q., Wu Y.-Q. and Abeies R.H, Biochem., 35, 3351 (1996).
- 6. Xing R and Hanzlik R.P., J. Med. Chem., 41, 1344 (1998).
- 7. Wieczerzak E., Drabik P., Lankiewicz L., Ołdziej S., Grzonka Z., Abrahamson M., Grubb A. and Brömme D., J. Med. Chem,, 45,4202, (2002).
- 8. Dutta A.S. and Morley J.S., J. Chem. Soc. Perkin I, 1712 (1975).
- 9. Ram S. and Ehrenkaufer R.E., Synthesis, 91 (1988).
- 10. Anwer M.K., Sherman D.B., Roney J.G. and Spatola A.F., J. Org. Chem., 54, 1284 (1989).
- 11. Rajagopal S. and Spatola A.F., J. Org. Chem., 60, 1347(1995).
- 12. Grehn L. and Ragnarsson U„ Tetrahedron, 55,4843 (1999).
- 13. Caiabretta R, Gallina C. and Giordano C., Synthesis, 536 (1991).
- 14. Gray C.J., Ireson J.C. and Parker R.C., Tetrahedron, 33, 739 (1977).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0021-0031