Towards a greener synthesis of (S)-3-aminobutanoic acid: Process development and environmental assessment

Green Chemistry

Volumn 12, Issue 9, 2010, Pages 1580-1588

  Weiß, Markus ^a   Brinkmann, Tobias ^b   Gröger, Harald ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b Ifu Hamburg GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CANDIDA ANTARCTICA;

EID: 77956375118     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c002721a     Document Type: Article

References (45)

1. E. Juaristi, (Ed.), Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York, 1997.
2. For reviews see: M. Liu M. P. Sibi Tetrahedron 2002 58 7991-8035.
3. A. Liljeblad L. T. Kanerva Tetrahedron 2006 62 5831-5854.
4. For selected chemocatalytic examples, see: Y. Hsiao N. R. Rivera T. Rosner S. W. Krska E. Njolito F. Wang Y. Sun J. D. Armstrong E. J. J. Grabowski R. D. Tillyer F. Spindler C. Malan J. Am. Chem. Soc. 2004 126 9918-9919.
5. A. Berkessel F. Cleemann S. Mukherjee Angew. Chem. 2005 117 7632-7635.
6. Angew. Chem., Int. Ed. 2005 44 7466-7469.
7. A. M. Clausen B. Dziadul K. L. Cappuccio M. Kaba C. Starbuck Y. Hsiao T. M. Dowling Org. Process Res. Dev. 2006 10 723-726.
8. M. Sibi K. Itoh J. Am. Chem. Soc. 2007 129 8064-8065.
9. For selected biocatalytic examples, see: S. G. Cohen S. Y. Weinstein J. Am. Chem. Soc. 1964 86 725-728.
10. V. A. Soloshonok V. K. Svedas V. P. Kukhar A. G. Kirilenko A. V. Rybakova V. A. Solodenko N. A. Fokina O. V. Kogut I. Y. Gulaev E. V. Kozlova I. P. Shishkina S. V. Galushko Synlett 1993 339-341.
11. M. Prashad D. Har O. Repic T. J. Blacklock P. Giannousis Tetrahedron: Asymmetry 1998 9 2133-2136.
12. G. Cardillo L. Gentilucci A. Tolomelli C. Tomasini J. Org. Chem. 1998 63 2351-2353.
13. S. Katayama N. Ae R. Nagata Tetrahedron: Asymmetry 1998 9 4295-4299.
14. S. J. Faulconbridge K. E. Holt L. G. Sevillano C. J. Lock P. D. Tiffin N. Tremayne S. Winter Tetrahedron Lett. 2000 41 2679-2681.
15. H. Gröger O. May H. Hüsken S. Georgeon K. Drauz K. Landfester Angew. Chem. 2006 118 1676-1679.
16. Angew. Chem., Int. Ed. 2006 45 1645-1648.
17. H. Gröger H. Trauthwein S. Buchholz K. Drauz C. Sacherer S. Godfrin H. Werner Org. Biomol. Chem. 2004 2 1977-1978 Reviews: ref. 2.
18. For selected efficient enzymatic enantioselective syntheses of aliphatic β-amino acids, see: R. Stürmer, K. Dietrich, W. Siegel, US Pat., 60636615, 2000.
19. Ref. 4b Reviews: ref. 2 M. Weiß H. Gröger Synlett 2009 8 1251-1254.
20. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, 1998, p. 30.
21. EATOS: environmental assessment tool for organic syntheses; this software has been developed in the Metzger group, see: M. Eissen J. O. Metzger Chem.–Eur. J. 2002 8 16 3580-3585.
22. This study has been performedwiththesoftware Umberto (version 5.5), which was complemented with data sets and ecological assessment tools from the software Sabento (version 1.2). These software programmes have been developed by ifu Hamburg GmbH, see: http://www.ifu.com.
23. For the EHS assessment the methodology of Heinzle was chosen, see: E. Heinzle, final report for the project AZ0312752A, German Federal Ministry of Education and Research.
24. The further developed methodology as implemented in Sabento is described in: T. Brinkmann H. Rubbeling P. Fröhlich M. Katzberg M. Bertau Chem. Eng. Technol. 2010 33 618.
25. R. A. Sheldon Chem. Ind. (London) 1992 6 903-906.
26. R. A. Sheldon Green Chem. 2007 9 1273-1283.
27. For an overview and comparison of ecological assessment tools, see: F. Eiden A. Schmid transcript 2008 14 29.
28. B. M. Trost Proc. Natl. Acad. Sci. U. S. A. 2008 105 13197-13202.
29. J. O. Metzger Angew. Chem. 1998 110 3145-3148.
30. Angew. Chem., Int. Ed. 1998 37 2975-2978.
31. K. Tanaka Chem. Rev. 2000 100 1025-1074.
32. I. T. Horvath Green Chem. 2008 10 1024-1028.
33. To remove traces of (R)-3-(benzylamino)butanoic acid (presumably formed via hydrolysis of rac-3 with residual water on immobilized CAL-B), the organic layer was extracted two times with an aqueous solution of NaOH (0.1 M, 1 mL).
34. http://www.dguv.de/bgia/de/gestis/stoffdb/index.jsp (checked 29.01.2010).
35. http://webnet3.oecd.org/echemportal (checked 29.01.2010).
36. http://cfpub.epa.gov/ecotox (checked 29.01.2010).
37. http://www.acros.com (checked 29.01.2010).
38. http://www.sigmaaldrich.com (checked 29.01.2010).
39. http://www.merck-chemicals.de (checked 29.01.2010).
40. M. Eissen, G. Geisler, B. Bühler, C. Fischer, K. Hungerbühler, A. Schmid, E. M. Carreira, in A. Lapkin, D. Constable, (Ed.), Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes, Wiley, Chichester UK, 2008, 200-227.
41. Although being aware that according to the concept of Sheldon (see ref. 10 and 11) water is typically not considered in the calculation of the E-value, in this work the amount of water from aqueous solutions has been considered in the calculation of the E-value by assuming a recycling rate of 90% of these solutions (which results in a higher E-value compared to the E-value without considering water from aqueous solutions).
42. The regeneration of the enzyme was tested over five cycles according to Table 2. From these experiments a recovery rate of 85% has been calculated.
43. −1) = 17.28 mL. As, for all other pure organic and aqueous solutions a recovery rate of 90% is assumed.
44. M. Nejman A. Sliwinska A. Zwierzak Tetrahedron 2005 61 8536-8541.
45. S. G. Davies A. W. Mulvaney A. J. Russell A. D. Smith Tetrahedron: Asymmetry 2007 18 1554-1566.