Continuous flow synthesis of α-halo ketones: Essential building blocks of antiretroviral agents

Journal of Organic Chemistry

Volumn 79, Issue 4, 2014, Pages 1555-1562

  Pinho, Vagner D ^a   Gutmann, Bernhard ^a   Miranda, Leandro S M ^b   De Souza, Rodrigo O M A ^b   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ANHYDRIDES; ANTI-RETROVIRAL AGENTS; DIAZOMETHANE; HIV PROTEASE INHIBITORS; HYDROCARBONS, HALOGENATED; KETONES; MOLECULAR STRUCTURE;

EID: 84894568743     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402849z     Document Type: Article

References (66)

1. Izawa, K.; Onishi, T. Chem. Rev. 2006, 106, 2811-2827
2. Wensing, A. M. J.; van Maarseveen, N. M.; Nijhuis, M. Antiviral Res. 2010, 85, 59-74
3. McKeage, K.; Perry, C. M.; Keam, S. J. Drugs 2009, 69, 477-503
4. WHO Model List of Essential Medicines, 18th list (April 2013), (Final Amendments, October 2013).
5. Goehring, W.; Gokhale, S.; Hilpert, H.; Roessler, F.; Schlageter, M.; Vogt, P. Chimia 1996, 50, 532-537
6. Chen, P.; Cheng, P. T. W.; Spergel, S. H.; Zahler, R.; Wang, X.; Thottathil, J.; Barrish, J. C.; Polniaszek, R. P. Tetrahedron Lett. 1997, 38, 3175-3178
7. Dufour, M.-N.; Jouin, P.; Poncet, J.; Pantaloni, A.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1986, 1895-1899
8. Patel, R. N.; Banerjee, A.; McNamee, C. G.; Brzozowski, D. B.; Szarka, L. J. Tetrahedron: Asymmetry 1997, 8, 2547-2554
9. Hamada, T.; Torii, T.; Onishi, T.; Izawa, K.; Ikariya, T. J. Org. Chem. 2004, 69, 7391-7394
10. Honda, Y.; Katayama, S.; Kojima, M.; Suzuki, T.; Kishibata, N.; Izawa, K. Org. Biomol. Chem. 2004, 14, 2061-2070
11. Barluenga, J.; Baragana, B.; Concellon, J. M. J. Org. Chem. 1995, 60, 6696-6699
12. Raddatz, P.; Jonczyk, A.; Minck, K.-O.; Schmitges, C. J.; Sombroek, J. J. Med. Chem. 1991, 34, 3267-3280
13. Patel, R. N.; Chu, L.; Mueller, R. Tetrahedron: Asymmetry 2003, 14, 3105-3109
14. Hoffman, R. V.; Weiner, W. S.; Maslouh, N. J. Org. Chem. 2001, 17, 5790-5795
15. Heinsoo, A.; Raidaru, G.; Linask, K.; Järv, J.; Zetterstrom, M.; Langel, Ü. Tetrahedron: Asymmetry 1995, 6, 2245-2247
16. Rotella, D. P. Tetrahedron Lett. 1995, 36, 5453-5456
17. Kaldor, S. W.; Kalish, V. J.; Davies, J. F., II; Shetty, B. V.; Fritz, J. E.; Appelt, K.; Burgess, J. A.; Campanale, K. M.; Chirgadze, N. Y.; Clawson, D. K.; Dressman, B. A.; Hatch, S. D.; Khalil, D. A.; Kosa, M. B.; Lubbehusen, P. P.; Muesing, M. A.; Patick, A. K.; Reich, S. H.; Su, K. S.; Tatlock, J. H. J. Med. Chem. 1997, 40, 3979-3985
18. Rotella, D. P. Tetrahedron Lett. 1995, 36, 5453-5456
19. For a continuous flow synthesis of α-diazo ketones from amino acids using trimethylsilyldiazomethane, see: 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
20. Black, T. H. Aldrichimica Acta 1983, 16, 3-22
21. Pizey, J. S. Synthetic Reagents; John Wiley & Sons: New York, 1974; Vol. 2, pp 65-142.
22. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160
23. Archibald, T. G.; Huang, D.-S.; Pratton, M. H.; Barnard, J. C. Large scale batch process for diazomethane. (Aerojet-General Corporation). U.S. Patent 5,817,778, 1998.
24. Archibald, T. G.; Barnard, J. C.; Harlan, R. F. Continuous process for diazomethane from an N-methyl-N-nitrosoamine and from methylurea through N-Methyl-N-nitrosourea. (Aerojet-General Corporation). U.S. Patent 5,854,405, 1998.
25. Proctor, L. D.; Warr, A. J. Org. Process Res. Dev. 2002, 6, 884-892
26. Poechlauer, P. Chim. Oggi 2012, 30, 51-54
27. Maurya, R. M.; Park, C. P.; Lee, L. H.; Kim, D.-P. Angew. Chem., Int. Ed. 2011, 50, 5952-5955
28. Mastronardi, F.; Gutmann, B.; Kappe, C. O. Org. Lett. 2013, 15, 5590-5593
29. Martin, L. J.; Marzinzik, A. L.; Ley, S. V.; Baxendale, I. R. Org. Lett. 2011, 13, 320-323
30. Rossi, E.; Woehl, P.; Maggini, M. Org. Process Res. Dev. 2012, 16, 1146-1149
31. Struempel, M.; Ondruschka, B.; Daute, R.; Stark, A. Green Chem. 2008, 10, 41-43
32. See also ref 7.
33. Hessel, V.; Kralisch, D.; Kockmann, N.; Noel, T.; Wang, Q. ChemSusChem 2013, 6, 746-789
34. Baxendale, I. R. J. Chem. Technol. Biotechnol. 2013, 88, 519-552
35. Newman, S. G.; Jensen, K. F. Green Chem. 2013, 15, 1456-1472
36. Wiles, C.; Watts, P. Green Chem. 2012, 14, 38-54
37. Noël, T.; Buchwald, S. L. Chem. Soc. Rev. 2011, 40, 5010-5029
38. Baumann, M.; Baxendale, I. R.; Ley, S. V. Mol. Diversity 2011, 15, 613-630
39. Yoshida, J.-i.; Kim, H.; Nagaki, A. ChemSusChem 2011, 4, 331-340
40. Baxendale, I. R.; Deeley, J.; Griffiths-Jones, C. M.; Ley, S. V.; Saaby, S.; Tranmer, G. K. Chem. Commun. 2006, 2566-2568
41. Bogdan, A. R.; Poe, S. L.; Kubis, D. C.; Broadwater, S. J.; McQuade, D. T. Angew. Chem., Int. Ed. 2009, 48, 8547-8550
42. Petersen, T. P.; Ritzén, A.; Ulven, T. Org. Lett. 2009, 11, 5134-5137
43. Lévesque, F.; Seeberger, P. H. Angew. Chem., Int. Ed. 2012, 51, 1706-1709
44. Hopkin, M. D.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem. 2013, 11, 1822-1839
45. Snead, D. R.; Jamison, T. F. Chem. Sci. 2013, 4, 2822-2827
46. 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
47. Longstreet, A. R.; Opalka, S. M.; Campbell, B. S.; Gupton, B. F.; McQuade, D. T. Beilstein J. Org. Chem. 2013, 9, 2570-2578
48. Dalla-Vechia, L.; Reichart, B.; Glasnov, T.; Miranda, L. S. M.; Kappe, C. O.; de Souza, R. O. M. A. Org. Biomol. Chem. 2013, 11, 6806-6813
49. The tube-in-tube device (gas addition module) is available from Uniqsis Ltd. See www.uniqsis.com for more details.
50. 3: O'Brien, M.; Baxendale, I. R.; Ley, S. V. Org. Lett. 2010, 12, 1596-1598
51. 2: Polyzos, A.; O'Brien, M.; Petersen, T. P.; Baxendale, I. R.; Ley, S. V. Angew. Chem., Int. Ed. 2011, 50, 1190-1193
52. CO: Koos, P.; Gross, U.; Polyzos, A.; O'Brian, M.; Baxendale, I.; Ley, S. V. Org. Biomol. Chem. 2011, 9, 6903-6908
53. 2: O'Brian, M.; Taylor, N.; Polyzos, A.; Baxendale, I. R.; Ley, S. V. Chem. Sci. 2011, 2, 1250-1257
54. Newton, S.; Ley, S. V.; Casas Arcé, E.; Grainger, D. M. Adv. Synth. Catal. 2012, 354, 1805-1812
55. 3: Cranwell, P. B.; O'Brian, M.; Browne, D. L.; Koos, P.; Polyzos, A.; Peña-Lopéz, M.; Ley, S. V. Org. Biomol. Chem. 2012, 10, 5774-5779
56. For an analysis of mass transfer and scalability of the tube-in-tube reactor, see: Yang, L.; Jensen, K. F. Org. Process Res. Dev. 2013, 17, 927-933
57. Generation of CO: Brancour, C.; Fukuyama, T.; Mukai, Y.; Skrydstrup, T.; Ryu, I. Org. Lett. 2013, 15, 2794-2797
58. Trifluoroacetic acid
59. Buba, A. E.; Koch, S.; Kunz, H.; Löwe, H. Eur. J. Org. Chem. 2013, 4509-4513
60. Struempel, M.; Ondruschka, B.; Stark, A. Org. Process Res. Dev. 2009, 13, 1014-1021
61. See also ref 12.
62. de Boer, T. J.; Backer, H. J. In Organic Syntheses; Wiley & Sons: New York, 1963; Collect. Vol. IV, pp 943-946.
63. Fittkau, S. H. J. Prakt. Chem. 1973, 315, 1037-1044
64. Bureš, F.; Kulhánek, J. Tetrahedron: Asymmetry. 2005, 7, 1347-1354
65. Wang, X.; Thottathil, J. K.; Polniaszek, R. P. Synlett 2000, 6, 902-904
66. Teno, N.; Wanaka, K.; Okada, Y.; Taguchi, H.; Okamoto, U.; Hijikata, A.; Okamoto, S. Chem. Pharm. Bull. 1993, 6, 1079-1090