Efficient synthesis of (S)-4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-ben zazepin-2-acetic acid (Pht-Hba(2,6,Cl2-Bn)-Gly-OH)

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6487-6492

  Casimir, J Richard ^a,b   Tourwé, Dirk ^a   Iterbeke, Koen ^a   Guichard, Gilles ^b   Briand, Jean Paul ^b  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 PHTHALIMIDO 1,3,4,5 TETRAHYDRO 8 (2,6 DICHLOROBENZYLOXY) 3 OXO 2H 2 BENZAZEPIN 2 ACETIC ACID; BENZAZEPINE DERIVATIVE; OXAZOLIDINE DERIVATIVE; PEPTIDE DERIVATIVE; STANNIC CHLORIDE; TRIFLUOROMETHANESULFONIC ACID; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CYCLIZATION; METHODOLOGY; REACTION ANALYSIS; SYNTHESIS;

BENZAZEPINES; DIPEPTIDES; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; PHTHALIMIDES; SUPPORT, NON-U.S. GOV'T;

EID: 0034613359     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000530d     Document Type: Article

References (25)

1. 2-Bn, 2,6-dichlorobenzyl; EI, electrospray ionization; EMM, exact mass measurement; GITC, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate; Hba, 4-amino-1,2,4,5-tetrahydro-8-hydroxy-2-benzazepin-3-one; HEL, hen egg lysozyme; HOBt, N-hydroxybenzotriazole; MHC, major histocompatibility complex; Pht, phthaloyl; TFA, trifluoroacetic acid; TFMSA, trifluoromethane sulfonic acid.
2. Warshawsky, A. M.; Flynn, G. A.; Koehl, J. R.; Mehdi, S. Bioorg. Med. Chem. Lett. 1996, 6, 957.
3. Mosberg, H. I.; Lomize, A. I.; Wang, C.; Kroona, H.; Heyl, D. L. J. Med. Chem. 1994, 37, 4371.
4. Flynn, G. A.; Giroux, E. L.; Dage, R. J. Am. Chem. Soc. 1987, 109, 9, 7914.
5. Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooks, J. R.; Saperstein R. Science 1980, 210, 656.
6. Hruby, V. J.; Li, G.; Haskell-Luevano, C. Biopolymers 1997, 43, 219.
7. Gibson, S. E.; Guillo, N.; Tozer, M. J. Tetrahedron 1999, 55, 585.
8. Hernandez, J. F.; Cretin, F.; Lombard-Platet, S.; Salvi, J. P.; Walchshofer, N.; Gerlier, D.; Paris, J.; Rabourdin-Combe, C. Peptides 1994, 15, 583.
9. Ettouati, L.; Casimir, J. R.; Raynaud, I.; Trescol-Biemont, M.-C.; Carrupt, P.-A.; Gerlier, D.; Rabourdin Combe, Ch.; Testa, B.; Paris, J. Prot. Pept. Lett. 1998, 5, 221.
10. Casimir J. R.; Trescol-Biémont, M.-C.; Tourwé, D.; Paris, J.; Ettouati, L.; Iterbeke, K.; Van Den Nest, W.; Gerlier, D.; Rabourdin-Combe, C. In Peptides 1998, Proceedings of the 25th European Peptide Symposium; Bajusz, S., Hudecz F., Eds.; Akadémiai Kiado: Budapest, 1999; p 654.
11. Tourwé, D.; Verschueren, K.; Frycia, A.; Davis, P.; Porreca, F.; Hruby, V. J.; Toth, G.; Jaspers, H.; Verheyden, P.; Van Binst, G. Biopolymers 1996, 38, 1.
12. Flynn, G. A.; Burkholder, T. P.; Huber, E. W.; Bey, P. Bioorg. Med. Chem. Lett. 1991, 6, 309.
13. de Laszlo, S. E.; Bush, B. L.; Doyle, J. J.; Greenlee, W. J.; Hangauer, D. G.; Halgren, T. A.; Lynch, R. J.; Schorn, T. W.; Siegl, P. K. S. J. Med. Chem. 1992, 35, 833.
14. Tourwé, D.; Verschueren, K.; Van Binst G.; Davis P.; Porreca F.; Hruby, V. J. Bioorg. Med. Chem. Lett. 1992, 2, 1305.
15. Almquist, R. G.; Olsen, C. M.; Uyeno, E. T.; Toll, L. J. Med. Chem. 1984, 27, 115.
16. Nimura, N.; Ogura, H.; Kinoshita, T. J. Chromatogr. 1980, 202, 375.
17. Sheehan, J. C.; Chapman, D. W.; Roth, R. W. J. Am. Chem. Soc. 1952, 74, 3822.
18. Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857.
19. Vitullo, V. P.; Grossman, N. J. Am. Chem. Soc. 1972, 94, 3844.
20. Vitullo, V. P. J. Org. Chem. 1968, 34, 224.
21. Erickson, B. W.; Merrifield, R. B. J. Am. Chem. Soc. 1973, 95, 3750.
22. Bodanszky, M.; Bodanszky, A. In The Practice of Peptide Synthesis; Hafner, K., Ed.; Springer-Verlag: Berlin, 1984; p 62.
23. Wünsch E.; Wendlberger G.; Jentsch J. Chem. Ber. 1964, 97, 8.
24. Tourwé, D.; Nikiforovich, G. V.; Iterbeke, K. In Peptides 1996, Proceedings of the 24th European Peptide Symposium; Ramage, R., Epton, R., Eds.; Mayflower: Kingswinford, 1998; p 835.
25. Tyler, A. N.; Clayton, E.; Green, B. N. Anal. Chem. 1996, 68, 3561.