Development of a sustainable catalytic ester amidation process

ACS Sustainable Chemistry and Engineering

Volumn 1, Issue 10, 2013, Pages 1339-1344

  Caldwell, Nicola ^a   Jamieson, Craig ^a   Simpson, Iain ^b   Watson, Allan J B ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Amidation; Design of Experiments; Green solvents; Reaction screening; Replacement bases

Indexed keywords

AMIDATION; CATALYTIC QUANTITIES; ESTER DERIVATIVES; GREEN SOLVENTS; OPTIMIZED CONDITIONS; POTASSIUM PHOSPHATE; REACTION CONDITIONS; REPLACEMENT BASES;

DESIGN OF EXPERIMENTS; ESTERIFICATION; OPTIMIZATION; SOLVENTS;

ESTERS;

EID: 84885340747     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400204g     Document Type: Article

References (34)

1. Peptides, Synthesis, Structures and Applications; Gutte, B., Ed.; Academic Press: San Diego, 1995.
2. Pattabiraman, V. R; Bode, J. W. Rethinking amide bond synthesis Nature 2011, 480, 471-479
3. Roughley, S. D.; Jordan, A. M. The Medicinal Chemist's Toolbox: An analysis of reactions used in the pursuit of drug candidates J. Med. Chem. 2011, 54, 3451-3479
4. Cooper, T. W. J.; Campbell, I. B; Macdonald, S. J. F. Factors determining the selection of organic reactions by medicinal chemists and the use of these reactions in arrays (small focused libraries) Angew. Chem., Int. Ed. 2010, 49, 8082-8091
5. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Analysis of the reactions used for the preparation of drug candidate molecules Org. Biomol. Chem. 2006, 4, 2337-2347
6. For a review see: El-Faham, A.; Albericio, F. Peptide coupling reagents, more than a letter soup Chem. Rev. 2011, 111, 6557-6602
7. Alfonsi, K.; Colberg, J.; Dunn, P. J.; Fevig, T.; Jennings, S.; Johnson, T. A.; Kleine, H. P.; Knight, C.; Nagy, M.A.; Perry, D. A.; Stefaniak, M. Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation Green Chem. 2008, 10, 31-36
8. Carpino, L. A. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive J. Am. Chem. Soc. 1993, 115, 4397-4398
9. Curzons, A. D.; Constable, D. J. C.; Mortimer, D. N.; Cunningham, V. L. So you think your process is green. How do you know?-Using principles of sustainability to determine what is green-A corporate perspective Green Chem. 2001, 3, 1-6
10. Sabot, C.; Kumar, K. A.; Meunier, S.; Mioskowski, C. A convenient aminolysis of esters catalysed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions Tetrahedron Lett. 2007, 48, 3863-3866
11. Arnold, K.; Batsanov, A. S.; Davies, B.; Whiting, A. Synthesis, evaluation and application of novel bifunctional N,N- di- isopropylbenzylamineboronic acid catalysts for direct amide formation between carboxylic acids and amines Green Chem. 2008, 10, 124-134
12. Allen, C. L.; Chhatwal, C. R.; Williams, J. M. J. Direct amide formation from unactivated carboxylic acids and amines Chem. Commun. 2012, 48, 666-668
13. Ghosh, S.; Bhaumik, A.; Mondal, J.; Mallik, A.; Sengupta, S.; Mukhopuahyay, C. Direct amide bond formation from carboxylic acids and amines using activated alumina balls as a new, convenient, clean, reusable and low cost heterogeneous catalyst Green Chem. 2012, 14, 3220-3229
14. Gernigon, N.; Al-Zoubi, R. M.; Hall, D. G. Direct amidation of carboxylic acids catalyzed by ortho -iodo arylboronic acids: Catalyst optimisation, scope and preliminary mechanistic study supporting a peculiar halogen acceleration effect J. Org. Chem. 2012, 77, 8386-8400
15. Ohshima, T. I.; Hayashi, Y.; Agura, K.; Fuji, Y.; Yoshiyama, A.; Mashima, K. Sodium methoxide: A simple but highly efficient catalyst for the direct amidation of esters Chem. Commun. 2012, 48, 5434-5436
16. Caldwell, N.; Jamieson, C.; Simpson, I.; Tuttle, T. Organobase-catalyzed amidation of esters with amino alcohols Org. Lett. 2013, 15, 2506-2509
17. MacMillan, D. S.; Murray, J.; Sneddon, H. F.; Jamieson, C.; Watson, A. J. B. Replacement of dichloromethane within chromatographic purification: A guide to alternative solvents Green Chem. 2012, 14, 3016-3019
18. MacMillan, D. S.; Murray, J.; Sneddon, H. F.; Jamieson, C.; Watson, A. J. B. Evaluation of alternative solvents in common amide coupling reactions: Replacement of dichloromethane and N,N- dimethylformamide Green Chem. 2013, 15, 596-600
19. McGonagle, F. I.; MacMillan, D. S.; Murray, J.; Sneddon, H. F.; Jamieson, C.; Watson, A. J. B. Development of a solvent selection guide for aldehyde-based direct reductive amination processes Green Chem. 2013, 15, 1159-1165
20. Schwesinger, R. Extremely strong, non-ionic bases: Syntheses and applications Chimia 1985, 39, 269
21. Adams, J. P.; Alder, C. M.; Andrews, I.; Bullion, A. M.; Campbell-Crawford, M.; Darcy, M. G.; Hayler, J. D.; Henderson, R. K.; Oare, C. A.; Pendrak, I.; Redman, A. M.; Shuster, L. E.; Sneddon, H. F.; Walker, M. D. Development of GSK's reagent guides-Embedding sustainability into reagent selection Green Chem. 2013, 15, 1542-1549
22. Frondel, C. Constitution and polymorphism of the pyroaurite and sjogrenite groups Am. Mineral. 1941, 26, 295-315
23. Jin, T.; Zhang, S.; Li, T. Transesterification of β-ketoesters with alcohols catalyzed by montmorillonite K-10 Green Chem. 2002, 4, 32-34
24. Constable, D. J. C.; Jimenez-Gonzalez, C.; Henderson, R. K. Perspective of solvent use in the pharmaceutical industry Org. Process Res. Dev. 2007, 11, 133-137
25. Henderson, R. K.; Jimenez-Gonzalez, C.; Constable, D. J. C.; Alston, S. R.; Inglis, G. G. A.; Fisher, G.; Sherwood, J.; Binks, S. P.; Curzons, A. D. Expanding GSK's solvent selection guide-Embedding sustainability into solvent selection starting at medicinal chemistry Green Chem. 2011, 13, 854-862
26. Elgue, S.; Prat, L.; Cabassund, M.; Cezerak, J. Optimisation of solvent replacement procedures according to economic and environmental criteria Chem. Eng. J. 2006, 117, 169-177
27. Gani, R. Chemical product design: Challenges and opportunities Comput. Chem. Eng. 2004, 28, 2441-2457
28. Antonucci, V.; Coleman, J.; Ferry, J. B.; Johnson, N.; Mathe, M.; Scott, J. P.; Xu, J. Toxicological assessment of 2-methyltetrahydrofuran and cyclopentyl methyl ether in support of their use in pharmaceutical chemical process development Org. Process Res. Dev. 2011, 15, 939-941
29. Watanabe, K.; Yamagiwa, N.; Torisawa, Y. Cyclopentyl methyl ether as a new and alternative process solvent Org. Process Res. Dev. 2007, 11, 251-258
30. Zeon Home Page. http://www.zeon.co.jp.
31. Winterberg, M.; Schulte-Korne, E.; Peters, U.; Nierlich, F. Methyl tert-Butyl Ether in Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Hoboken, NJ, 2010.
32. Methyl Tertiary Butyl Ether (MTBE). U.S. Environmental Protection Agency. http://www.epa.gov/mtbe.
33. Grundy, R. D. Strategies for control of man-made eutrophication Environ. Sci. Technol. 1971, 5, 1185-1190
34. Carlson, R. Design and Optimization in Organic Synthesis; Elsevier: Amsterdam, 1992; Chapter 2.