Development of a fully telescoped synthesis of the S1P1 agonist GSK1842799

Organic Process Research and Development

Volumn 15, Issue 3, 2011, Pages 649-659

  Anson, Michael S ^a   Graham, Jonathan P ^a   Roberts, Alastair J ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE METABOLITES; DRUG SUBSTANCES; KEY FEATURE; LAWESSON'S REAGENTS; NUCLEOPHILIC AROMATIC SUBSTITUTION; SALT FORMATION; THIADIAZOLES;

PHOSPHORYLATION;

EID: 79957476299     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op2000095     Document Type: Article

References (25)

1. Evindar, G.; Deng, H.; Bernier, S.; Yao, G.; Coffin, A.; Yang, H. WO/2008/016692, 2008.
2. Anson, M. S.; Day, C. J.; Graham, J. P.; Kindon, L. J.; Woolham, G. R. WO/2009/098193, 2009.
3. For a recent review on S1P1 agonists, see Cusack, K. P.; Stoffel, R. H. Curr. Opin. Drug Discovery Dev. 2010, 13, 481
4. Initial discovery and preparation of GSK1842799 was performed by Praecis Pharmaceuticals, Inc., and multigram preparations of 1 were performed under contract by Albany Molecular Research, Inc.
5. For a review on the use of fluorous tags in chemical synthesis, see Zhang, W. Chem. Rev. 2009, 109, 749
6. Wender, P. A.; Miller, B. L. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; Jai Press: Greenwich, 1993; Vol. 2, pp 27 - 66
7. Wender, P. A. Chem. Rev. 1996, 96, 1
8. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174
9. For a review on the concept of self-regeneration of stereocentres, see Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. 1996, 35, 2708
10. Decomposition of the lithium enolate of methyl (2 R,4 S)-2-(1,1-dimethylethyl)-3-formyl-1,3-oxazolidine-4-carboxylate has been noted even at -78 °C, see Seebach, D.; Aebi, J. D. Tetrahedron Lett. 1984, 25, 2545
11. Reinheimer, J. D.; Kieffer, W. F.; Frey, S. W.; Cochran, J. C.; Barr, E. W. J. Am. Chem. Soc. 1958, 80, 164
12. For reviews on the synthesis of α,α-disubstituted α-amino acids, see Vogt, H.; Bräse, S. Org. Biomol. Chem. 2007, 5, 406
13. Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127
14. With, T. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley: Weinheim, 2000; pp 26 - 33.
15. For a review on the synthesis of 2-methylserine, see Nakano, K.; Kotsuki, H.; Ichikawa, Y. Org. Prep. Proced. Int. 2008, 40, 67
16. Anson, M. S.; Clark, H. F.; Evans, P.; Fox, M. E.; Graham, J. P.; Griffiths, N. N.; Meek, G.; Ramsden, J. A.; Roberts, A. J.; Simmonds, S.; Walker, M. D.; Willets, M. Org. Process Res. Dev. 2011, 10.1021/op100299d.
17. Jones, M. A.; Hislop, A. D.; Snaith, J. S. Org. Biomol. Chem. 2006, 4, 3769
18. Chirotech Technology, Ltd., A subsidiary of Dr. Reddy's Laboratories (EU) Ltd.
19. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194
20. Brunner, M.; Saarenketo, P.; Straub, T.; Rissanen, K.; Koskinen, A. M. P. Eur. J. Org. Chem. 2004, 3879-3883
21. For recent reviews on Lawesson's reagent, see Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210
22. Jesberger, M.; Davis, T. P.; Barner, L. Synthesis 2003, 13, 1929
23. Rasmussen, P. B.; Pedersen, U.; Thomsen, I.; Yde, B.; Lawesson, S.-O. Bull. Soc. Chim. Fr. 1985, 62
24. Aycook, D. F. Org. Process Res. Dev. 2007, 11, 156
25. Teasdale, A.; Eyley, S. C.; Delaney, E.; Jacq, K.; Taylor-Worth, K.; Lipczynski, A.; Reif, V.; Elder, D. P.; Facchine, K. L.; Golec, S.; Oestrich, R. S.; Sandra, P.; David, F. Org. Process Res. Dev. 2009, 13, 429