Continuous-flow synthesis and purification of atropine with sequential in-line separations of structurally similar impurities

Journal of Flow Chemistry

Volumn 5, Issue 3, 2015, Pages 133-138

  Dai, Chunhui ^a   Snead, David R ^a   Zhang, Ping ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Atropine; Continuous flow synthesis; Membrane separation

Indexed keywords

EID: 84956642806     PISSN: 2062249X     EISSN: 20630212     Source Type: Journal    
DOI: 10.1556/1846.2015.00013     Document Type: Article

References (45)

1. Plouffe, P.; Macchi, A. Org. Proc. Res. Dev. 2014, 18, 1286-1294.
2. Manson, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 2300-2318.
3. Anderson, N. G. Org. Proc. Res. Dev. 2012, 16, 852-869.
4. Plumb, K. Chem. Eng. Res. Des. 2005, 83, 730-738.
5. Longstreet, A. R.; Opalka, S. M.; Campbell, B. S.; Gupton, B. F.; McQuade, D. T. Beilstein J. Org. Chem. 2013, 9, 2570-2578.
6. Rodrigues, T.; Schneider, P.; Schneider, G. Angew. Chem., Int. Ed. 2014, 53, 5750-5758.
7. Pinho, V. D.; Gutmann, B.; Miranda, L. S. M.; de Souza, R. O. M. A.; Kappe, C. O. J. Org. Chem. 2014, 79, 1555-1562.
8. Ghislieri, D.; Gilmore, K.; Seeberger, P. H. Angew. Chem., Int. Ed. 2015, 54, 678-682.
9. Bogdan, A. R.; Poe, S. L.; Kubis, D. C.; Broadwater, C. J.; McQuade, D. T. Angew. Chem., Int. Ed. 2009, 48, 8547-8550.
10. Lévesque, F.; Seeberger, P. H. Angew. Chem., Int. Ed. 2012, 51, 1706-1709.
11. Battilocchio, C.; Deadman, B. J.; Nikbin, N.; Kitching, M. O.; Baxendale, I. R.; Ley, S. V. Chem. Eur. J. 2013, 19, 7917-7930.
12. Newton, S.; Carter, C. F.; Pearson, C.M.; Alves, L. de C.; Lange, H.; Thansandote, P.; Ley, S. V. Angew. Chem., Int. Ed. 2014, 53, 4915-4920.
13. Sahoo, H. R.; Kralj, J. G.; Jensen, K. F. Angew. Chem., Int. Ed. 2007, 46, 5704-5708.
14. Hartman, R. L.; Naber, J. R.; Buchwald, S. L.; Jensen, K. F. Angew. Chem., Int. Ed. 2010, 49, 899-903.
15. Noël, T.; Kuhn, S.; Musacchio, A. J.; Jensen, K. F.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 5943-5946.
16. Snead, D. R.; Jamison, T. F. Chem. Sci. 2013, 4, 2822-2827.
17. 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.
18. Heider, P. L.; Born, S. C.; Basak, S.; Benyahia, B.; Lakerveld, R.; Zhang, H.; Hogan, R.; Buchbinder, L.; Wolfe, A.; Mascia, S.; Evans, J. M. B.; Jamison, T. F.; Jensen, K. F. Org. Proc. Res. Dev. 2014, 18, 402-409.
19. Ingham, R. J.; Battilocchio, C.; Fitzpatrick, D. E.; Sliwinski, E.; Hawkins, J. M.; Ley, S. V. Angew. Chem., Int. Ed. 2015, 54, 144-148.
20. Vural Gürsel, I.; Aldiansyah, F.; Wang, Q.; Noël, T.; Hessel, V. Chem. Eng. J. 2015, 270, 468-475.
21. Adamo, A.; Heider, P. L.; Weeranoppanant, N.; Jensen, K. F. Ind. Eng. Chem. Res. 2013, 52, 10802-10808.
22. Hopkin, M. D.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem. 2013, 11, 1822-1839.
23. Hartman, R. L.; Sahoo, H. R.; Yen, B. C.; Jensen, K. F. Lab Chip, 2009, 9, 1843-1849.
24. O'Brien, A. G.; Horváth, Z.; Lévesque, F.; Lee, J.W.; Seidel-Morgenstern, A.; Seeberger, P. H. Angew. Chem., Int. Ed. 2012, 51, 7028-7030.
25. Polster, C. S.; Cole, K. P.; Burcham, C. L.; Campbell, B.M.; Frederick, A. L.; Hansen, M. M.; Harding, M.; Heller, M. R.; Miller, M. T.; Phillips, J. L.; Pollock, P. M.; Zaborenko, N. Org. Proc. Res. Dev. 2014, 18, 1295-1309.
26. Snead, D. R.; Jamison, T. F. Angew. Chem., Int. Ed. 2015, 54, 983-987.
27. Zhang, P.; Russell, M.G.; Jamison, T. F. Org. Proc. Res. Dev. 2014, 18, 1567-1570.
28. Vardanyan, R.; Hruby. V. J. Synthesis of Essential Drugs, 1st ed.; Elsevier Science: Amsterdam, 2006; p. 196.
29. WHO Model List of Essential Medicines: http://www.who.int/medicines/ publications/essentialmedicines/en/ (accessed Feb 8, 2015).
30. Gadzikowska, M.; Grynkiewicz, G. Acta Pol. Pharm. 2002, 59, 149-160.
31. Landenburg, A. Ber. 1879, 12, 941-944.
32. Robinson, R. J. Chem. Soc., Trans. 1917, 111, 762-768.
33. Gore, V.; Joshi, R.; Tripathi, A.; Jadhav, M.; Bhandari, S. Mylan Laboratories Ltd., Hyderabad, India. US Patent 2014/102829 Al, 2014.
34. Grynkiewicz, G.; Gadzikowska, M. Pharmacol. Rep. 2008, 60, 439-463.
35. Takeuchi, Y.; Koga, K.; Shioiri, T.; Yamada, S.-I. Chem. Pharm. Bull. 1971, 19, 2603-2608.
36. Trost, B. M.; Haffner, C. D.; Jebaratnam, D. J.; Krische, M. J.; Thomas, A. P. J. Am. Chem. Soc. 1999, 121, 6183-6192.
37. Li, Y.; Feng, J.-P.; Wang, W.-H.; Chen, J.; Cao, X.-P. J. Org. Chem. 2007, 72, 2344-2350.
38. Sharpe, R. J.; Malinowski, J. T.; Johnson, J. S. J. Am. Chem. Soc. 2013, 135, 17990-17998.
39. Rodriguez, L.; Lu, N.; Yang, N-L. Synlett, 1990, 4, 227-228.
40. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.
41. pH Buffers were made according to "Laboratory stock solution and equipment, common stock solutions, buffers, and media." Curr. Protoc. Cell Biol. 1998 Appendix 2: Appendix 2A. Solution A: 27.2 g KH2PO4 per liter in water. Solution B: 34.8 g K2HPO4 per liter in water. Thus, pH=8 buffer [0.1 M]: 5.3 mL (solution A) / 94.7 mL (solution B).
42. The boronic acid resin-packed cartridge needs to be replaced every 1.5 h in order to achieve complete removal of apoatropine.
43. Stenberg, V. I.; Narain, N. K.; Singh, S. P. J. Heterocycl. Chem. 1977, 14, 225-226.
44. Do Pham, D. D.; Kelso, G. F.; Yang, Y.; Hearn, M. T. W. Green Chem. 2012, 14, 1189-1195.
45. Taha, A. M.; Rücker, G. J. Pharm. Sci. 1978, 67, 775-779.