Development of a multi-step synthesis and workup sequence for an integrated, continuous manufacturing process of a pharmaceutical

Organic Process Research and Development

Volumn 18, Issue 3, 2014, Pages 402-409

  Heider, Patrick L ^a   Born, Stephen C ^a   Basak, Soubir ^a   Benyahia, Brahim ^a   Lakerveld, Richard ^a   Zhang, Haitao ^a   Hogan, Rachael ^a   Buchbinder, Louis ^a   Wolfe, Aaron ^a   Mascia, Salvatore ^a   Evans, James M B ^a   Jamison, Timothy F ^b   Jensen, Klavs F ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY;

ACTIVE PHARMACEUTICAL INGREDIENTS; CLOSED-LOOP CONTROL; CONTINUOUS MANUFACTURING; CONTINUOUS MANUFACTURING PROCESS; DEVELOPMENT AND OPERATIONS; LIQUID-LIQUID EXTRACTION; LOWER TEMPERATURES; PROCESS DISTURBANCES;

SYNTHESIS (CHEMICAL);

EID: 84896953509     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op400294z     Document Type: Article

References (42)

1. Poechlauer, P.; Manley, J.; Broxterman, R.; Gregertsen, B.; Ridemark, M. Org. Process Res. Dev. 2012, 16, 1586-1590
2. Evans, J. Chem. Eng. J. 2013, 32-34
3. DiMasi, J. A.; Hansen, R. W.; Grabowski, H. G. Journal of Health Economics 2003, 22, 151-185
4. Suresh, P.; Basu, P. J. Pharm. Innov. 2008, 3, 175-187
5. Federsel, H.-J. Acc. Chem. Res. 2009, 42, 671-680
6. Malet-Sanz, L.; Susanne, F. J. Med. Chem. 2012, 55, 4062-4098
7. Poechlauer, P.; Colberg, J.; Fisher, E.; Jansen, M.; Johnson, M. D.; Koenig, S. G.; Lawler, M.; Laporte, T.; Manley, J.; Martin, B.; O'Kearney-McMullan, A. Org. Process Res. Dev. 2013, 17, 1472-1478
8. Roberge, D. M.; Zimmermann, B.; Rainone, F.; Gottsponer, M.; Eyholzer, M.; Kockmann, N. Org. Process Res. Dev. 2008, 12, 905-910
9. Benaskar, F.; Ben-Abdelmoumen, A.; Patil, N.; Rebrov, E.; Meuldijk, J.; Hulshof, L.; Hessel, V.; Krtschil, U.; Schouten, J. J. Flow Chem. 2011, 1, 74-89
10. Schaber, S. D.; Gerogiorgis, D. I.; Ramachandran, R.; Evans, J. M. B.; Barton, P. I.; Trout, B. L. Ind. Eng. Chem. Res. 2011, 50, 10083-10092
11. Jiménez-González, C.; Poechlauer, P.; Broxterman, Q. B.; Yang, B.-S.; am Ende, D.; Baird, J.; Bertsch, C.; Hannah, R. E.; Dell'Orco, P.; Noorman, H.; Yee, S.; Reintjens, R.; Wells, A.; Massonneau, V.; Manley, J. Org. Process Res. Dev. 2011, 15, 900-911
12. Roberge, D. M.; Ducry, L.; Bieler, N.; Cretton, P.; Zimmermann, B. Chem. Eng. Technol. 2005, 28, 318-323
13. Webb, D.; Jamison, T. F. Chem. Sci. 2010, 1, 675-680
14. Wegner, J.; Ceylan, S.; Kirschning, A. Chem. Commun. 2011, 47, 4583-4592
15. Hartman, R. L.; McMullen, J. P.; Jensen, K. F. Angew. Chem., Int. Ed. 2011, 50, 7502-7519
16. Hessel, V. Chem. Eng. Technol. 2009, 32, 1655-1681
17. Sahoo, H. R.; Kralj, J. G.; Jensen, K. F. Angew. Chem., Int. Ed. 2007, 46, 5704-5708
18. Pollet, P.; Cope, E. D.; Kassner, M. K.; Charney, R.; Terett, S. H.; Richman, K. W.; Dubay, W.; Stringer, J.; Eckert, C. A.; Liotta, C. L. Ind. Eng. Chem. Res. 2009, 48, 7032-7036
19. Bogdan, A. R.; Poe, S. L.; Kubis, D. C.; Broadwater, S. J.; McQuade, D. T. Angew. Chem., Int. Ed. 2009, 48, 8547-8550
20. Li, P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 6396-6400
21. Johnson, M. D.; May, S. A.; Calvin, J. R.; Remacle, J.; Stout, J. R.; Diseroad, W. D.; Zaborenko, N.; Haeberle, B. D.; Sun, W.-M.; Miller, M. T.; Brennan, J. Org. Process Res. Dev. 2012, 16, 1017-1038
22. Cervera-Padrell, A. E.; Morthensen, S. T.; Lewandowski, D. J.; Skovby, T.; Kiil, S.; Gernaey, K. V. Org. Process Res. Dev. 2012, 16, 888-900
23. Hu, D. X.; O'Brien, M.; Ley, S. V. Org. Lett. 2012, 14, 4246-4249
24. Christensen, K. M.; Pedersen, M. J.; Dam-Johansen, K.; Holm, T. L.; Skovby, T.; Kiil, S. Chem. Eng. Sci. 2012, 71, 111-117
25. Wegner, J.; Ceylan, S.; Kirschning, A. Adv. Synth. Catal. 2012, 354, 17-57
26. Cervera-Padrell, A. E.; Skovby, T.; Kiil, S.; Gani, R.; Gernaey, K. V. Eur. J. Pharm. Biopharm. 2012, 82, 437-456
27. Mascia, S.; Heider, P. L.; Zhang, H.; Lakerveld, R.; Benyahia, B.; Barton, P. I.; Braatz, R. D.; Cooney, C. L.; Evans, J. M. B.; Jamison, T. F.; Jensen, K. F.; Myerson, A. S.; Trout, B. L. Angew. Chem., Int. Ed. 2013, 52, 12359-12363
28. Benyahia, B.; Lakerveld, R.; Barton, P. I. Ind. Eng. Chem. Res. 2012, 51, 15393-15412
29. Lakerveld, R.; Benyahia, B.; Braatz, R. D.; Barton, P. I. AIChE J. 2013, 59, 3671-3685
30. Foley, M. A.; Jamison, T. F. Org. Process Res. Dev. 2010, 14, 1177-1181
31. Rúeger, H.; Stutz, S.; Göschke, R.; Spindler, F.; Maibaum, J. Tetrahedron Lett. 2000, 41, 10085-10089
32. Sandham, D. A.; Taylor, R. J.; Carey, J. S.; Fássler, A. Tetrahedron Lett. 2000, 41, 10091-10094
33. Dondoni, A.; De Lathauwer, G.; Perrone, D. Tetrahedron Lett. 2001, 42, 4819-4823
34. Hanessian, S.; Guesné, S.; Chénard, E. Org. Lett. 2010, 12, 1816-1819
35. Levenspiel, O. Chemical Reaction Engineering; 3 rd ed.; John Wiley & Sons: New York, 1999.
36. Ananthakrishnan, V.; Gill, W. N.; Barduhn, A. J. AIChE J. 1965, 11, 1063-1072
37. Kralj, J. G.; Sahoo, H. R.; Jensen, K. F. Lab Chip 2007, 7, 256-263
38. Aota, A.; Mawatari, K.; Takahashi, S.; Matsumoto, T.; Kanda, K.; Anraku, R.; Hibara, A.; Tokeshi, M.; Kitamori, T. Microchim. Acta 2009, 164, 249-255
39. Castell, O. K.; Allender, C. J.; Barrow, D. A. Lab Chip 2009, 9, 388-396
40. Zhang, H.; Quon, J.; Alvarez, A. J.; Evans, J.; Myerson, A. S.; Trout, B. Org. Process Res. Dev. 2012, 16, 915-924
41. Lakerveld, R.; Benyahia, B.; Heider, P.; Zhang, H.; Braatz, R.; Barton, P. Processes 2013, 1, 330-348
42. Quon, J. L.; Zhang, H.; Alvarez, A.; Evans, J.; Myerson, A. S.; Trout, B. L. Cryst. Growth Des. 2012, 12, 3036-3044.