Development of a continuous Schotten-Baumann route to an acyl sulfonamide

Organic Process Research and Development

Volumn 16, Issue 5, 2012, Pages 939-957

  White, Timothy D ^a   Berglund, K Derek ^a   Groh, Jennifer McClary ^a   Johnson, Martin D ^a   Miller, Richard D ^a   Yates, Matthew H ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; BATCH PROCESS; CONTINUOUS PROCESS; CONTINUOUS PROCESSING; CYTOTOXIC; FUME HOODS; PROOF OF CONCEPT; REACTION CONDITIONS; SCALE-UP; SODIUM SALT; SYNTHETIC ROUTES; WORKER EXPOSURE;

BATCH DATA PROCESSING; CHLORINE COMPOUNDS; FUME CONTROL; SODIUM; THIOPHENE;

SALTS;

EID: 84862098779     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200344a     Document Type: Article

References (47)

1. Wegner, J.; Ceylan, S.; Kirschning, A. Adv. Synth. Catal. 2012, 354, 17-57
2. Brocklehurst, C. E.; Lehmann, H.; La Vecchia, L. Org. Process Res. Dev. 2011, 15, 1447-1453
3. Brandt, J. C.; Elmore, S. C.; Robinson, R. I.; Wirth, T. Synlett 2010, 3099-3013
4. Delville, M. M. E.; Nieuwland, P. J.; Janssen, P.; Koch, K.; van Hest, J. C. M.; Rutjes, F. P. J. T. Chem. Eng. J. 2011, 167, 556-559
5. Palde, P. B.; Jamison, T. F. Angew. Chem., Int. Ed. 2011, 50, 3525-3528
6. Proctor, L.; Dunn, P. J.; Hawkins, J. M.; Wells, A. S.; Williams, M. T. In Green Chemistry in the Pharmaceutical Industry; Dunn, P. J.; Wells, A. S.; Williams, M. T., Eds.; Wiley-VCH: Weinheim, 2010; pp 221-242.
7. Zotova, N.; Hellgardt, K.; Kelsall, G. H.; Jessiman, A. S.; Hii, K. K. Green Chem. 2010, 12, 2157-2163
8. Rode, C. V.; Ghalwadkar, A. A.; Mane, R. B.; Hengne, A. M.; Jadkar, S. T.; Biradar, N. S. Org. Process Res. Dev. 2010, 14, 1385-1392
9. Riva, E.; Gagliardi, S.; Martinelli, M.; Passarella, D.; Vigo, D.; Rencurosi, A. Tetrahedron 2010, 66, 3242-3247
10. Ye, X; Johnson, M. D.; Diao, T.; Yates, M. H.; Stahl, S. S. Green Chem. 2010, 12, 1180-1186
11. Tilstam, U.; Defrance, T.; Giard, T.; Johsnson, M. D. Org. Process Res. Dev. 2009, 13, 321-323
12. Hessel, V.; Cortese, B.; de Croon, M. H. J. M. Chem. Eng. Sci. 2011, 66, 1426-1448
13. Strategic Plan for Regulatory Science. Advancing Regulatory Science at FDA; U.S. Department of Health and Human Services, Food and Drug Administration: Rockville, MD, 2011.
14. ICH Q8 Pharmaceutical Development, (R2); U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER): Rockville, MD, Aug 2009.
15. Myerson, A. S. Handbook of Industrial Crystallisations; Butterworth-Heinemann: Boston, 2002.
16. Randolph, A. D.; Larson, M. A. Theory of Particulate Processes: Analysis and Techniques of Continuous Crystallization; Academic Press: New York, 1988.
17. Mullin., J. W. Crystallization, 4 th ed.; Butterworth-Heinemann: Woburn, MA, 2001.
18. Jones, A. G. Crystallization Process Systems; Butterworth-Heinemann: Woburn, MA, 2002.
19. Eder, R. J. P.; Radl, S; Schmitt, E; Innerhofer, S.; Maier, M.; Gruber-Woelfler, H.; Khinast, J. G. Cryst. Growth Des. 2010, 10, 2247-2257
20. Alvarez, A. J.; Myerson, A. S. Cryst Growth Des. 2010, 10, 2219-2228
21. Lawton, S.; Steele, G.; Shering, P.; Zhao, L.; Laird, I.; Ni, X. Org. Process Res. Dev. 2009, 13, 1357-1363
22. Alvarez, A.; Singh, A.; Myerson, A. S. Cryst Growth Des. 2011, 11, 4392-4400
23. Kougoulos, E.; Jones, A. G.; Wood-Kaczmar, M. W. J. Cryst. Growth 2005, 273, 520-528
24. Kougoulos, E; Jones, A. G.; Jennings, K. H.; Wood-Kaczmar, M. W. J. Cryst. Growth 2005, 273, 529-534
25. Van Alsten, J. G.; Reeder, L. M.; Stanchina, C. L.; Knoechel, D. J. Org. Process Res. Dev. 2008, 12, 989
26. Chen, J.; Sarma, B; Evans, J. M. B.; Myerson, A. S. Cryst Growth Des. 2011, 11, 887-895
27. Asakuma, Y.; Tetahima, T.; Maeda, K.; Hideo, M.; Fukeu, D. Powder Technol. 2007, 171, 75-80
28. Miki, H.; Fukunaga, R.; Asakuma, Y.; Maeda, K.; Fukui, K. Sep. Purif. Technol. 2005, 43, 77-83
29. Miki, H.; Terashima, T.; Asakuma, Y.; Maeda, K.; Fukui, K. Sep. Purif. Technol. 2005, 43, 71-76
30. Rauls, M.; Bartosch, K.; Kind, M.; Kuch, St.; Lacmann, R.; Mersmann, A. J. Cryst. Growth 2000, 213, 116-128
31. Chan, V. A.; Ang, H. M. J. Cryst. Growth 1996, 166, 1009-1014
32. Tanrikulu, S. U.; Eroglu, I.; Bulutcu, A. N.; Ozkar, S. J. Cryst. Growth 2000, 208, 533-540
33. De Dios, A.; Grossman, C. S.; Hipskind, P. A.; Lin, H. S.; Lobb, K. L.; Lopez De Uralde Garmendia, B.; Lopez, J. E.; Mader, M. M.; Richett, M. E.; Shih, C. WO/2003/035629, 2003.
34. Lobb, K. L.; Hipskind, P. A.; Aikins, J. A.; Alvarez, E.; Cheung, Y.; Considine, E. L.; De Dios, A.; Durst, G. L.; Ferritto, R.; Grossman, C. S.; Giera, D. D.; Hollister, B. A.; Huang, Z.; Iversen, P. W.; Law, K. L.; Li, T.; Lin, H.; Lopez, B.; Lopez, J. E.; Cabrejas, L. M. M.; McCann, D. J.; Molero, V.; Reilly, J. E.; Richett, M. E.; Shih, C.; Teicher, B.; Wikel, J. H.; White, W. T.; Mader, M. J. Med. Chem. 2004, 47, 5367-5380
35. Mader, M. M.; Shih, C.; Considine, E.; De Dios, A.; Grossman, C. S.; Hipskind, P. A.; Lin, H.; Lobb, K. L.; Lopez, B.; Lopez, J. E.; Cabrejas, L. M. M.; Richett, M. E.; White, W. T.; Cheung, Y.; Huang, Z.; Reilly, J. E.; Dinn, S. R. Bioorg. Med. Chem. Lett. 2005, 15, 617-620
36. White, T. D.; Berglund, K. D.; Groh, J. M.; Johnson, M. D.; Yates, M. H. Development of a Continuous Process for Tasisulam Sodium. Flow Chemistry Congress, Boston, MA, USA, 28 - 29 April, 2011.
37. Yates, M. H.; Kallman, N. J.; Ley, C. P.; Wei, J. N. Org. Process Res. Dev. 2009, 13, 255-262
38. Wankat, P. Separations in Chemical Engineering Equilibrium Staged Separations; PTR Prentice Hall: New York, 1988; p 520.
39. Ripin, D. H. B.; Vetelino, M. Synlett 2003, 2353
40. neMESYS pumps were utilized for these additions: http://www.cetoni.de/ englisch/products/syringepump-nemesys-technic.html.
41. http://www.emerson.com/en-US/Pages/Default.aspx.
42. Braden, T. M.; Gonzalez, M. A.; Jines, A. M.; Johnson, M. D.; Sun, W.-M. Reactors and methods for processing reactants therein. WO/2009/023515, CAN 150:216733. 2009
43. Fogler, H. S. Elements of Chemical Reaction Engineering, 3rd ed.; Prentice Hall PTR: Upper Saddle River, NJ, 1999.
44. The success of the large-scale version of the gravity overflow resulted in the design of a small-scale version that has been presented at the Denver ACS: White, T. D.; Berglund, K. D.; Groh, J. M.; Johnson, M. D.; Yates, M. H. Development of a Continuous Schotten-Baumann Route to an Acyl Sulfonamide. Abstracts of Papers; 242nd ACS National Meeting and Exposition, Denver, CO, United States, August 28-September 1, 2011.
45. Atlas pumps were utilized for this addition: http://www.syrris.com/batch- products/atlas-syringe-pump
46. The tubing that was chosen for evaluation was L/S High-Performance Precision GORE STA-PURE (http://www.masterflex.com) with 1/4 in. ID and 1/16 in. wall thickness due to known compatibility with organic solvents. The compatibility with the extraction solvent system (4:1:2.5 v:v isopropyl acetate/2-MeTHF/toluene) was tested by running the mixture through the tubing for 55 h and performing gravimetric analysis of the blank solvent system compared to the solvent that had recycled through the system. No evidence of leachables was observed, and the tubing showed no evidence of breakdown.
47. FloPRo sampler utilized to collect samples during the extraction unit operation. See http://www.globalfia.com/.