Rearrangement of the active ester intermediate during HOBt/EDC amide coupling

European Journal of Inorganic Chemistry

Volumn , Issue 1, 2005, Pages 173-180

  Mahmoud, Khaled A ^a   Long, Yi Tao ^a   Schatte, Gabriele ^b   Kraatz, Heinz Bernhard ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Amide coupling; Amino acid; Electrochemistry; Ferrocene; Hydroxybenzotriazole

Indexed keywords

AMIDES; CARBOXYLATION; ESTERS; HYDROGEN BONDS; IRON COMPOUNDS; ORGANOMETALLICS; SPECTROSCOPIC ANALYSIS; X RAY CRYSTALLOGRAPHY;

ACTIVE ESTERS; AMIDE COUPLINGS; AMINO-ACIDS; BENZOTRIAZOLES; FERROCENES; HYDROXYBENZOTRIAZOLE; N-OXIDES; NON-POLAR SOLVENTS; PEPTIDE COUPLING; [CARBONYL;

AMINO ACIDS;

1 HYDROXYBENZOTRIAZOLE; 3 [[1' (TERT BUTYLOXYCARBONYLAMINO)FERROCEN 1 YL]CARBONYL]BENZOTRIAZOLE 1 OXIDE; AMIDE; BENZOTRIAZOL 1 YL 1' (TERT BUTYLOXYCARBONYLAMINO)FERROCENE 1 CARBOXYLATE; BENZOTRIAZOLE DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; FERROCENE DERIVATIVE; GLYCINE ETHYL ESTER; SOLVENT; UNCLASSIFIED DRUG; URETHAN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; ELECTRON; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; X RAY CRYSTALLOGRAPHY;

EID: 12344315084     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200400504     Document Type: Article

References (28)

1. W. Konig, R. Geiger, Chem. Ber. 1970, 103, 788.
2. S. I. Murahashi, H. Mitsui, T. Watanabe, S. I. Zenki, Tetrahedron Lett. 1983, 24, 1049.
3. R. Bosch, G. Jung, W. Winter, Acta Chyst. 1983, C39, 1089.
4. F. T. Boyle, R. A. Y. Jones, J. Chem. Soc., Perkin Trans. 1973, 2, 160.
5. J. Singh, R. Fox, M. Wong, T. P. Kissick, J. I. Moniot, J. Org. Chem. 1988, 53, 205.
6. J. S. Davies, A. K. Mohammed, J. Chem. Soc., Perkin Trans. 1981, 1, 2982.
7. K. Lu, S. Kumaresan, Y. Wen, J. R. Hwu, Organometallics 1994, 13, 3170.
8. F. Alain, J. Elguero, A. F. Hegarty, D. G. McCarthy, Org. Magn. Reson. 1980, 13, 339.
9. E. Anders, A. R. Katritzky, N. Malhotra, J. Stevens, J. Org. Chem. 1992, 57, 3698.
10. L. A. Carpino, H. Imazumi, A. El-Faham, Angew. Chem. Int. Ed. 2002, 41, 441.
11. D. R. v. Staveren, T. Weyhermuller, N. Metzler-Nolte, Dalton Trans. 2003, 210.
12. V. P. Andreev, A. V. Ryzhakov, Khim. Geterotsikl. Soedin. 1993, 12, 1662.
13. T. Okamura, K. Sakauye, N. Ueyama, A. Nakamura, Inorg. Chem. 1998, 37, 6731.
14. K. Heinze, M. Schlenker, Eur. J. Inorg. Chem. 2004, 2053.
15. H.-B. Kraatz, J. Lusztyk, G. D. Enright, Inorg. Chem. 1997, 36, 2400.
16. P. Mamos, D. Papaioannou, C. Kavounis, V. Nastopoulos, Acta Crystallogr., Sect. B 1997, 53, 1973.
17. K. Barlos, D. Papaioannou, D. Theodoropoulos, Int. J. Peptide Protein Res. 1984, 23, 300.
18. K. Barlos, D. Papaioannou, S. Voliotis, R. Prewo, J. Bieri, J. Org. Chem. 1985, 50, 696.
19. M. Crisma, G. Valle, V. Moretto, F. Formaggio, C. Toniolo, Lett. Pept. Sci. 1998, 5, 247.
20. C. Toniolo, M. Crisma, F. Formaggio, Biopolymers (Pept. Sci.) 1996, 40, 627.
21. E. S. Stevens, N. Sugawara, G. M. Bonora, C. Toniolo, J. Am. Chem. Soc. 1980, 102, 7048.
22. N. Metzler-Nolte, private communication.
23. L. Barisic, V. Kovac, Croat. Chem. Acta 2002, 75, 199.
24. COLLECT data collection software, N. B.V., 1998.
25. H. D. SCALEPACK, W. M. v1.96: Z. Otwinowski, Processing of X-ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology, vol. 276 (Macromolecular Crystallography, part A) (Eds.: C. W. Carter, Jr., R. M., Sweet); Academic Press, San Diego, CA, 1997.
26. A. Alatomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
27. G. M. Sheldrick, SHELXS-97, University of Göttingen, Göttingen, Germany, 1997.
28. G. M. Sheldrick, Program for the Solution of Crystal Structures; University of Göttingen, Göttingen, Germany, 1997.