Microwave-Assisted Synthesis Utilizing Supported Reagents: A Rapid and Efficient Acylation Procedure

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4721-4724

  Sauer, Daryl R ^a   Kalvin, Douglas ^a   Phelan, Kathleen M ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBOXYLIC ACID DERIVATIVE; POLYMER;

ACYLATION; ARTICLE; HEATING; MICROWAVE RADIATION; SYNTHESIS;

EID: 0348041985     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0358915     Document Type: Article

References (25)

1. For recent examples see: (a) Senten, K.; Danieels, L.; Van der Veken, P. ; De Meester, I.; Lambeir, A.-M.; Scharpe, S.; Haemers, A.; Augustyns, K. J. Comb. Chem. 2003, 5, 336-344. (b) South, M. S.; Dice, T. A.; Girard, T. J.; Lachance, R. M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2363-2367. (c) South, M. S.; Case, B. L.; Wood, R. S.; Jones, D. E.; Hayes, M. J.; Girard, T. J.; Lachance, R. M.; Nicholson, N. S.; Clare, M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2319-2325. (d) Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166-1170. (e) Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 2419-2422. (f) Yun, Y. K.; Porco, J. A., Jr.; Labadie, J. Synlett 2002, 739-742.
2. For recent examples see: (a) Senten, K.; Danieels, L.; Van der Veken, P. ; De Meester, I.; Lambeir, A.-M.; Scharpe, S.; Haemers, A.; Augustyns, K. J. Comb. Chem. 2003, 5, 336-344. (b) South, M. S.; Dice, T. A.; Girard, T. J.; Lachance, R. M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2363-2367. (c) South, M. S.; Case, B. L.; Wood, R. S.; Jones, D. E.; Hayes, M. J.; Girard, T. J.; Lachance, R. M.; Nicholson, N. S.; Clare, M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2319-2325. (d) Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166-1170. (e) Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 2419-2422. (f) Yun, Y. K.; Porco, J. A., Jr.; Labadie, J. Synlett 2002, 739-742.
3. For recent examples see: (a) Senten, K.; Danieels, L.; Van der Veken, P. ; De Meester, I.; Lambeir, A.-M.; Scharpe, S.; Haemers, A.; Augustyns, K. J. Comb. Chem. 2003, 5, 336-344. (b) South, M. S.; Dice, T. A.; Girard, T. J.; Lachance, R. M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2363-2367. (c) South, M. S.; Case, B. L.; Wood, R. S.; Jones, D. E.; Hayes, M. J.; Girard, T. J.; Lachance, R. M.; Nicholson, N. S.; Clare, M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2319-2325. (d) Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166-1170. (e) Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 2419-2422. (f) Yun, Y. K.; Porco, J. A., Jr.; Labadie, J. Synlett 2002, 739-742.
4. For recent examples see: (a) Senten, K.; Danieels, L.; Van der Veken, P. ; De Meester, I.; Lambeir, A.-M.; Scharpe, S.; Haemers, A.; Augustyns, K. J. Comb. Chem. 2003, 5, 336-344. (b) South, M. S.; Dice, T. A.; Girard, T. J.; Lachance, R. M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2363-2367. (c) South, M. S.; Case, B. L.; Wood, R. S.; Jones, D. E.; Hayes, M. J.; Girard, T. J.; Lachance, R. M.; Nicholson, N. S.; Clare, M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2319-2325. (d) Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166-1170. (e) Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 2419-2422. (f) Yun, Y. K.; Porco, J. A., Jr.; Labadie, J. Synlett 2002, 739-742.
5. For recent examples see: (a) Senten, K.; Danieels, L.; Van der Veken, P. ; De Meester, I.; Lambeir, A.-M.; Scharpe, S.; Haemers, A.; Augustyns, K. J. Comb. Chem. 2003, 5, 336-344. (b) South, M. S.; Dice, T. A.; Girard, T. J.; Lachance, R. M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2363-2367. (c) South, M. S.; Case, B. L.; Wood, R. S.; Jones, D. E.; Hayes, M. J.; Girard, T. J.; Lachance, R. M.; Nicholson, N. S.; Clare, M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2319-2325. (d) Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166-1170. (e) Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 2419-2422. (f) Yun, Y. K.; Porco, J. A., Jr.; Labadie, J. Synlett 2002, 739-742.
6. For recent examples see: (a) Senten, K.; Danieels, L.; Van der Veken, P. ; De Meester, I.; Lambeir, A.-M.; Scharpe, S.; Haemers, A.; Augustyns, K. J. Comb. Chem. 2003, 5, 336-344. (b) South, M. S.; Dice, T. A.; Girard, T. J.; Lachance, R. M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2363-2367. (c) South, M. S.; Case, B. L.; Wood, R. S.; Jones, D. E.; Hayes, M. J.; Girard, T. J.; Lachance, R. M.; Nicholson, N. S.; Clare, M.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; Parlow, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 2319-2325. (d) Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166-1170. (e) Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 2419-2422. (f) Yun, Y. K.; Porco, J. A., Jr.; Labadie, J. Synlett 2002, 739-742.
7. (a) Flynn, D. L.; Devraj, R. V.; Naing, W.; Parlow, J. J.; Weidner, J. J.; Yang, S. Med. Chem. Res. 1998, 8, 219-243.
8. (b) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Dis. Dev. 1998, 1, 41-50.
9. (c) Weidner, J. J.; Parlow, J. J.; Flynn, D. L. Tetrahedron Lett. 1999, 40, 239-242.
10. Argonaut Technologies, http://www.argotech.com.
11. 13C NMR, and HRMS.
12. Lannuzel, M.; Lamothe, M.; Perez, M. Tetrahedron Lett. 2001, 42, 6703-6705.
13. Jamieson, C.; Congreve, M. S.; Emiabata-Smith, D. F.; Ley, S. V. Synlett 2000, 1603-1607.
14. South, M. S.; Dice, T. A.; Parlow, J. J. Biotechnol. Bioeng. 2000, 71, 51-57.
15. (a) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
16. (b) Kappe, C. O. Curr. Opin. Chem. Bio. 2002, 6, 314-320.
17. (c) Dzierba, C. D.; Combs, A. P. Annu. Rep. Med. Chem. 2002, 37, 247-256.
18. (d) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283.
19. (e) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251-1255.
20. The reaction of DCM and HOBt has been observed at ambient temperature after extended periods of time: Ji, J.-G.; Zhang, D.-Y.; Ye, Y.-H.; Xing, Q.-Y. Tetrahedron Lett. 1998, 39, 6515-6516.
21. All microwave reactions were performed on an Emrys Optimizer (Personal Chemistry, http://www.personalchemistry.com) without the use of continuous cooling. Wattage was automatically adjusted so as to maintain the desired temperature.
22. Stadler, A.; Kappe, C. O. Eur. J. Org. Chem. 2001, 919-925.
23. Weidner, J. J.; Parlow, J. J.; Flynn, D. L. Tetrahedron Lett. 1999, 40, 239-242.
24. SiliCycle, Inc., http://www.silicycle.com
25. General Procedure for the Preparation of Amides via Microwave Heating and Si-Carbonate SPE. A Smith Process Vial (2-5 mL) was charged with a stir bar and 200 mg of PS-carbodiimide resin (1.2 mmol/g). To the vessel were added 1 (21 mg, 0.12 mmol) in NMP (0.7 mL), HOBt (16 mg, 0.12 mmol) in NMP (0.7 mL), and benzylamine (13 mg, 0.12 mmol) in NMP (0.7 mL). The reaction vessel was sealed and heated to 100°C for 5 min in an Emrys Optimizer. After cooling the vessel was uncapped and the reaction mixture diluted with 2 mL of MeOH. The reaction mixture was transferred via pipet to a pre-packed column of Si-Carbonate (1 g, 0.7 mmol/g), which had been previously conditioned with MeOH, and the elutant collected via gravity filtration. The column was washed with MeOH (2 x 3 mL) and the solvent evaporated at reduced pressure to afford 2 (31 mg, 98%) as a white solid that was 98% pure by LC/MS analysis.