Solid-phase synthesis of substituted glutamic acid derivatives via Michael addition reactions

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2167-2170

  Domínguez, Esteban ^a   O'Donnell, Martin J ^b   Scott, William L ^c  

^a ELI LILLY AND COMPANY   (Spain)

^b INDIANA UNIVERSITY   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMATE RECEPTOR; GLUTAMIC ACID DERIVATIVE;

ARTICLE; DERIVATIZATION; SYNTHESIS;

EID: 0032499139     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00165-8     Document Type: Article

References (15)

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2. (b) Gordon, E. M.; Barret, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
3. (c) Ecker, D. J.; Crooke, S. T. Biotechnology 1995, 13, 351.
4. (d) Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
5. (e) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
6. (f) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
7. 2. Unnatural amino acid and peptide synthesis for the preparation of mono-substituted derivatives (UPS): (a) O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070.
8. (b) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163.
9. 3. Unnatural amino acid and peptide synthesis for the preparation of α,α-disubstituted derivatives (di-UPS): Scott, W. L.; Zhou, C.; Fang, Z.; O'Donnell, M. J. Tetrahedron Lett. 1997, 38, 3695.
10. 4. (a) Wermuth, C. G.; Man, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D, D. J. Med. Chem. 1996, 39, 814.
11. (b) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreño, M. C.; Escribano, A.; García Ruano, J. L. J. Org. Chem. 1995, 60, 2925 and references cited therein.
12. (c) Lodge, D. in "Excitatory Amino Acids in Health and Disease", John Wiley & Sons, Inc.: New York, 1988.
13. 3CN (solvent B) with a gradient of 0-80% B over 20 min at a flow rate of 1 mL/min and detection at 240 nm.
14. 6. Experimental procedure for more reactive Michael acceptors (cases 8h-8j): See note 5 for general conditions. 5 to 6: Resin 5, BEMP (3.0 eq), Michael acceptor (1.0 eq), NMP (1.5 mL), 1h (for 8h and 8j). Resin 5, BEMP (3.0 eq), Michael acceptor (1.5 eq), NMP (1.5 mL), 88h (for 8i).
15. 7. Experimental procedure for less reactive Michael acceptors (cases 8k-8o): See note 5 for general conditions. 5 to 6: Resin 5, BEMP (10.0 eq), Michael acceptor (10.0 eq), NMP (1.5 mL), 16h.