Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin)

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1509-1514

  Hulme, Christopher ^a   Ma, Liang ^a   Kumar, N Vasant ^a   Krolikowski, Paul H ^a   Allen, Andrew C ^a   Labaudiniere, Richard ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALDEHYDE DERIVATIVE; ALPHA AMINO ACID; ANTHRANILIC ACID DERIVATIVE; BENZODIAZEPINE DERIVATIVE; KETOPIPERAZINE; PIPERAZINE DERIVATIVE; RESIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034603431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02326-6     Document Type: Article

References (40)

1. Armstrong, R. W.; Brown, S. D.; Keating, T. A.; Tempest, P. A. In Combinatorial chemistry. Synthesis and Application; Wilson, S. R.; Czarnik, A. W., Eds.; John Wiley: New York, 1997; pp. 153-190.
2. (a) Ugi, I. Angew. Chem., Int. Ed. Engl. 1962, 1, 8.
3. (b) Ugi, I.; Steinbruckner, C. Chem Ber. 1961, 94, 734.
4. (c) Ugi, I.; Domling, A.; Horl, W. Endeavor 1994, 18, 115.
5. Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227.
6. Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751.
7. (a) Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943.
8. (b) Short, K. M.; Ching, B. W.; Mjalli, A. M. M. Tetrahedron 1997, 53, 6653.
9. (c) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
10. (a) Blackburn, C.; Guan, B.; Fleming, P.; Shiosaki, K.; Tsai, S. Tetrahedron Lett. 1998, 39, 3635.
11. (b) Bienayme, H.; Bouzid, K. Angew. Chem., Int. Ed. 1998, 37, 2234.
12. (c) Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672.
13. (d) Park, S.-J.; Keum, G.; Kang, S.-B.; Koh, H.-Y.; Kim, Y. Tetrahedron Lett. 1998, 39, 7109.
14. (a) Domling, A. Combinatorial Chemistry & High Throughput Screening, 1998, 1.
15. (b) Keating, T. A.; Armstrong, R. W. J. Org. Chem. 1996, 61, 8935.
16. (c) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842.
17. (d) Rosendahl, F. K.; Ugi, I. Ann. Chem. 1963, 666, 65.
18. (e) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
19. Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573.
20. (a) McDowell, R. S.; Blackburn, B. K.; Gadek, T. R.; McGee, L. R.; Rawson, T.; Reynolds, M. E.; Robarge, K. D.; Somers, T. C.; Thorsett, E. D.; Tischler, M.; Webb, R. R.; Venuti, M. C. J. Am. Chem. Soc. 1994, 116, 5077.
21. (b) Cho, N. S.; Song, K. Y.; Parkanyi, C. J. Heterocycl. Chem. 1989, 26, 1807.
22. (c) Takada, S.; Kurokawa, T.; Miyazaki, K.; Iwasa, S.; Ogawa, Y. Pharm. Res. 1997, 14, 1146.
23. (d) Wright, H. B.; Martin, D. L. J. Med. Chem. 1968, 11, 390.
24. (e) Piercey, M. F.; Moon, M. W.; Blinn, J. R. Brain Res. 1986, 385, 74.
25. (a) Hulme, C.; Tang, S.-Y.; Burns, C. J.; Morize, I.; Labaudiniere, R. J. Org. Chem. 1998, 63, 8021.
26. (b) Hulme, C.; Peng, J.; Louridas, B.; Menard, P.; Krolikowski, P.; Kumar, N. V. Tetrahedron Lett. 1998, 39, 8047.
27. (c) Hulme, C.; Morrissette, M.; Volz, F.; Burns, C. Tetrahedron Lett. 1998, 39, 1113.
28. Wang bound Fmoc-α-amino acids were purchased from Advanced Chem-tech™.
29. N-BOC anthranilic acids are readily accessible in multi-gram quantities via the synthetic route shown below from the corresponding anthranilic acid or isatin. N-BOC diamines are readily available as described in: Krapcho, A. P.; Maresh, M. J.; Lunn, J. Synth. Comm. 1993, 23, 2443. A series of functionalized N-BOC anthranilic acids were prepared by Medichem Research, Inc for this project.
30. Note: Evaporation at elevated temperatures (or the use of higher percentage TFA solutions) leads to hydrolysis of the isonitrile-derived amide bond giving the corresponding carboxylic acid.
31. A series of N-BOC-α-amino-aldehydes are commercially available from BACHEM™.
32. 3CN to 100% over 5 min. HPLC was interfaced with APCI techniques.
33. 3). The sample consisted of two diastereomers in approximately 3:1 ratio and most of the critical resonances were well resolved under the present experimental conditions. DQFCOSY spectra of both the diastereomers showed three independent spin systems (-CH-CH2,-NH-CH2 and-CH-CH2-CH2 fragments) in addition to the aromatic spin systems. HMBC spectra showed numerous three-bond connectivities supporting the structure shown for the compound 8.
34. (a) Gilbert, I.; Rees, D. C.; Richardson, R. S. Tetrahedron Lett. 1991, 32, 2277.
35. (b) Jones, R. C. F.; Ward, G. J. Tetrahedron Lett. 1988, 29, 3853.
36. (a) Pigini, M.; Bousquet, P.; Carotti, A.; Dontenwill, M.; Gianella, M.; Moriconi, R.; Piergentili, A.; Quaglia, W.; Tayebati, S. K.; Brasili, L. Bioorg. Med. Chem. 1997, 5, 833.
37. (b) Harfenist, M.; Heuser, D. J.; Joyner, C. T.; Batchelor, J. F.; White, H. L. J. Med. Chem. 1996, 39, 1857.
38. (c) Jackson, H. C.; Griffin, I. J.; Nutt, D. J. Br. J. Pharmacol. 1991, 104, 258.
39. (d) Tibirica, E.; Feldman, J.; Mermet, C.; Gonon, F.; Bousquet, P. J. Pharmacol. 1987, 134, 1.
40. Hulme, C.; Ma, L.; Romano, J.; Morrissette, M. Tetrahedron Lett. 1999, 40, 7925.