Addition of HOAt dramatically improves the effectiveness of pentafluorophenyl-based coupling reagents

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2045-2048

  Klose, J ^a   El Faham, A ^a,b   Henklein, P ^a,c   Carpino, L A ^a,b   Bienert, M ^a  

^a LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

^c HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 7 AZABENZOTRIAZOLE; 1 HYDROXYPENTAFLUOROPHENYL; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OLIGOMERIZATION;

EID: 0033548689     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00089-1     Document Type: Article

References (18)

1. Wen, J.J.; Spatola, A.F. J. Peptide Res., 1997, 49, 3.
2. Gordon, E.M.; Barett, R.W.; Dower, W.J.; Fodor, S.P.A., Gallop, M.A. J. Med. Chem., 1994, 27, 1385.
3. Abbreviations: DIEA: N,N-diisopropylethylamine; DMF: dimethylformamide; HAPyTU: S-(7-azabenzotriazol-l-yl)-1,1:3,3-bis(tetramethylene)thiouronium hexafluorophosphate; HAPyU: 1-(1-pyrrolidinyl)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene)pyrrolidinium hexafluorophosphate N-oxide; HATTU: S-(7-azabenzotriazol-l-yl)-1,1:3,3-tetramethyl-thiouronium hexafluorophosphate; HATU: N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethyIene]-N-methylmethanaminium hexafluorophosphate N-oxide; HOAt: 1-hydroxy-7-azabenzotriazole; HOPfp: pentafluorphenol; HPyOPfp: O-(pentafluorophenyl)-1,1:3,3-bis(tetramethylene)uronium hexafluorophosphate; HPySPfp: S-(pentafluorophenyl)-1,1:3,3-bis(tetramethylene)thiouronium hexafluorophosphate;PyAOP: (7-aza-benzotriazol-l-yloxy)tris(pyrrolidino)phosphonium hexafluorophosphate; PyPfpOP: (pentafluorophenoxy)tris(pyrrolodino)phosphonium hexafluorophosphate; TMP: 2,4,6-trimethylpyridine.
4. Carpino, L.A.; El-Faham, A.; Minor, C.A.; Albericio, F. J. Chem. Soc., Chem. Comm., 1994, 201.
5. Carpino, L.A. J. Am. Chem. Soc., 1993, 115, 4397.
6. Ehrlich, A.; Rothemund, S.; Brudel, M.; Beyermann, M.; Carpino, L.A.; Bienert, M. Tetrahedron Lett., 1993, 34, 4781.
7. Ehrlich, A.; Heyne, H.-U.; Winter, R.; Beyermann, M.; Haber, H.; Carpino, L.A.; Bienert, M. J. Org. Chem., 1996, 61, 8831.
8. Henklein, P.; Carpino, L.A.. unpublished.
9. Habermann, J.; Kunz, H. Tetrahedron Lett., 1998, 39, 265.
10. Since no definitive X-ray crystallography data are available for any thiolated derivatives of HAPyU and HATU they are arbitrarily named here as the uronium species.
11. for preparation of coupling reagents see also a) Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett., 1989, 30, 1927.
12. b) Echner, H; Voelter, W. Poster "rapid thioester couplings mediated by new uronium salts"presented at the 5th Meeting on "Innovation and Perspectives in Solid Phase Synthesis", London, 1997.
13. a) Carpino, L.A.; El-Faham, A.; Albericio, F. J. Org. Chem., 1995, 60, 3561.
14. b) Carpino, L.A.; El-Faham, A. J. Org. Chem., submitted for publication, 1998.
15. Klose, J.; El-Faham, A.; Henklein, P.; Carpino, L.A.; Bienert, M. in: Proceedings of the 25th European Peptide Symposium, Budapest, 1998, in press.
16. a) Akaji, K.; Kuriyama, N.; Kiso, Y. J. Org. Chem., 1996, 61, 3350.
17. b) El-Faham, A. J. Org. Chem., 1996, 61, 2460.
18. c) El-Faham, A. OPPI, 1998, 30, 477.