Expeditious synthesis of Mosher amides using a solid supported carbodiimide

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7171-7172

  Adamczyk, Maciej ^a   Fishpaugh, Jeffrey R ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030607187     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01617-6     Document Type: Article

References (20)

1. 1. a) Stinson, S.C. Chemistry & Engineering News 1995, 73(41), 44.
2. b) Cannarsa, M.J. Chem. Ind. 1996, 374.
3. 2. a) Dale, J.A., Dull, D.L. and Mosher H.S. J. Org. Chem. 1969, 34, 2543.
4. b) Yamaguchi, S. in Asymmetric Synthesis (Morrison, J. ed.), 1983, Vol. 1, Ch. 7, 125-142.
5. 1H NMR, see Dale, J.A. and Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512.
6. 19F NMR, see Sullivan, G.R.; Dale, J.A. and Mosher, H.S. J. Org. Chem. 1973, 38, 2143.
7. 4. LeBelle, M.J.; Savard, C.; Dawson, B.A.; Black, D.B.; Katyal, L.K.; Zrcek, F. and By, A.W. Forensic Sci. Int. 1995, 77, 215.
8. 5. Balani, S. et al. J. Chem. Soc., Perkin Trans. I. 1983, 2751.
9. 6. Kusumi, T.; Fukushima, T.; Ohtani, I. and Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939.
10. 7. Erikson, S.D.; Simon, J.A. and Still, W.C. J. Org. Chem. 1993, 58, 1305.
11. 8. Ward, D.E. and Rhee, C.K. Tetrahedron Lett. 1991, 32, 7165.
12. 9. a) Kabuto, K.; Yasuhara, F. and Yamaguchi, S. Tetrahedron Lett. 1981, 22, 659.
13. b) Evans, D.A.; Britton, T.C.; Durow, R.L. and Dellaria, J.F. Tetrahedron 1988, 44, 5525.
14. 10. Desai, M. and Stramiello, L. Tetrahedron Lett. 1993, 34, 7685.
15. 11. Adamczyk, M.; Fishpaugh, J. and Mattingly, P. Tetrahedron Lett. 1995, 36, 8345.
16. 12. Adamczyk, M. and Fishpaugh, J. Tetrahedron Lett. 1996, 37, 0000.
17. 1H NMR.
18. 14. Coupling of a chiral secondary alcohol under these conditions gave only the starting alcohol and none of the desired ester. Additives employed afforded only mixtures of desired ester and starting alcohol.
19. 3, filtered and vacuum dried to remove any residual non-deuterated solvents prior to use.
20. 16. All amides had correct molecular weight by MS and were >97% purity by analytical HPLC (analytical μporasil column eluted with ethyl acetate/hexanes).