Reaction of α-(n-alkylcarbonyloxy)alkyl (ACOA) halides with 4-hydroxyacetanilide and 2,2,5,7,8-pentamethyl-6-chromanol: The effect of steric hindrance on reaction path

Synthesis

Volumn , Issue 2, 2008, Pages 272-278

  Thomas, Joshua D ^a   Sloan, Kenneth B ^a  

^a UNIVERSITY OF FLORIDA HEALTH   (United States)

Author keywords

Acylation; Alkyl halides; Alkylation; Phenols; Steric hindrance

Indexed keywords

ACYLATION; DERIVATIVES; PHENOLS; REACTION KINETICS; TOXICITY;

ALKYL HALIDES; STERIC HINDRANCE;

FLUORIDE MINERALS;

6 HYDROXY 2,2,5,7,8 PENTAMETHYLCHROMAN; HALIDE; IODINE DERIVATIVE; PARACETAMOL; PHENOL DERIVATIVE;

ACYLATION; ALKYLATION; ARTICLE; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING OPENING; STEREOSPECIFICITY;

EID: 38849178103     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000858     Document Type: Article

References (35)

1. Bodor, N.; Sloan, K. B. US Patent 4061753, Chem. Abstr. 1977, 87, 152278.
2. Sloan, K. B.; Wasdo, S. Med. Res. Rev. 2003, 23, 763.
3. Mollgaard, B.; Hoelgaard, A.; Bundgaard, H. Int. J. Pharm. 1982, 12, 153.
4. Roberts, W.; Sloan, K. B. J. Pharm. Sci. 2003, 92, 1028.
5. Rautio, J.; Nevalainen, T.; Taipale, H.; Vepsalainen, J.; Gynther, J.; Laine, K.; Jarvinen, T. J. Med. Chem. 2000, 43, 1489.
6. Stinchcomb, A. L.; Swaan, P.; Ekabo, O.; Harris, K.; Browe, J.; Hammell, D.; Cooperman, T.; Pearsall, M. J. Pharm. Sci. 2002, 91, 2571.
7. Abbas, A.; Fadel, P.; Wang, Z.; Arbique, D.; Jialal, I.; Vongpatanasin, W. Arterioscler. Thromb. Vasc. Biol. 2004, 24, e164.
8. Thomas, J. D.; Sloan, K. B. Int. J. Pharm. 2007, 346, 80.
9. Brass, E. Pharmacol. Rev. 2002, 54, 589.
10. Tabbache, S.; Loubinoux, B. Synthesis 1982, 665.
11. Sloan, K. B.; Koch, S. J. Org. Chem. 1983, 48, 3777.
12. Ouyang, H.; Borchardt, R.; Siahaan, T. Tetrahedron Lett. 2002, 43, 577.
13. Thomas, J.; Sloan, K. B. Tetrahedron Lett. 2006, 47, 8785.
14. Iyer, R.; Yu, D.; Ho, N.; Agrawal, S. Synth. Commun. 1995, 25, 2739.
15. Binderup, E.; Hansen, E. T. Synth. Commun. 1984, 14, 857.
16. Thomas, J. D. Ph.D. Thesis; University of Florida: USA, 2006.
17. 2 were generally 20% lower than those shown.
18. Bundgaard, H.; Klixbull, U.; Falch, E. Int. J. Pharm. 1986, 30, 111.
19. Bensel, N.; Reymond, M.; Reymond, J. Chem. Eur. J. 2001, 7, 4604.
20. Charton, M. J. Am. Chem. Soc. 1975, 97, 1552.
21. Ramesh, C.; Mahender, G.; Ravindranath, N.; Das, B. Tetrahedron 2003, 59, 1049.
22. Blay, G.; Cardona, M.; Garcia, M.; Pedro, J. Synthesis 1989, 438.
23. Kunesch, N.; Miet, C.; Poisson, J. Tetrahedron Lett. 1987, 28, 3569.
24. Bell, K. Tetrahedron Lett. 1986, 27, 2263.
25. Chakraborti, A.; Sharma, L.; Sharma, U. Tetrahedron 2001, 57, 9343.
26. Datta, A.; Hepperle, M.; Georg, G. J. Org. Chem. 1995, 60, 761.
27. Roberts, W.; Sloan, K. B. J. Heterocycl. Chem. 2002, 39, 905.
28. Fairbrother, J. In Analytical Profiles of Drug Substances, Vol. 3; Florey, K., Ed.; Academic Press: New York, 1974, 1-110.
29. McClelland, R.; Kanagasabapathy, V. M.; Mathivanan, N. Can. J. Chem. 1991, 69, 2084.
30. Nagase and co-workers have used a similar procedure for deprotecting 1-benzyloxycarbonyloxymethyl-5-fluorouracil: Nasage, T.; Seike, K.; Shiraishi, K.; Yamada, Y.; Ozaki, S. Chem. Lett. 1988, 1381.
31. Smith, M.; March, J. In March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; Smith, M.; March, J., Eds.; Wiley: New York, 2001, 5th ed., 389-675.
32. Sloan, K. B.; Koch, S. J. Org. Chem. 1983, 48, 635.
33. Charton, M. J. Org. Chem. 1978, 43, 3995.
34. Beaumont, K.; Webster, R.; Gardner, I.; Dack, K. Curr. Drug Metab. 2003, 4, 461.
35. Bauguess, C. T.; Sadik, F.; Fincher, J. H.; Hartman, C. W. J. Pharm. Sci. 1975, 64, 117.