Neopentyl ester protecting groups for arylsulfonic acids

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 355-358

  Roberts, John C ^a,b   Huai, Gao ^a   Gopalsamy, Ariamala ^a   Kongsjahju, Azis ^a   Patch, Raymond J ^a  

^a Procept Inc   (United States)

^b EISAI INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0343329890     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02302-7     Document Type: Article

References (13)

1. Richman, J. E.; Atkins, T. J. J. Am. Chem. Soc. 1974, 96, 2268.
2. Klamann, D.; Hofbauer, G. Ber. Deutsch. Chem. Ges. 1953, 86, 1246.
3. Plattner, J. J.; Marcotte, P. A.; Kleinert, H. D.; Stein, H. H.; Greer, J.; Bolis, G.; Fung, A. K. L.; Bopp, B. A.; Luly, J. R.; Sham, H. L.; Kempf, D. J.; Rosenberg, S. H.; Dellaria, J. F.; De, B.; Merits, I; Perun, T. J. J. Med. Chem. 1988, 31, 2277.
4. Dannley, R. L.; Corbett, G. E. J. Org. Chem. 1966, 31, 153.
5. (a) Musicki, B.; Widlanski, T. S. J. Org. Chem. 1990, 55, 4231.
6. (b) Musicki, B.; Widlanski, T. S. Tetrahedron Lett. 1991, 32, 1267.
7. Arduini, A.; Brilli, A.; Pavan, F.; Pochini, A.; Ungaro, R.; Corno, C. Tetrahedron 1990, 46, 3607.
8. Naphthyl reagents 4 (5,2-and 8,2-substituted) and phenyl reagents 4a (meta-and para-substituted) have been used in these studies. Whereas sterically congested dinaphthyl alcohols 6 underwent facile dehydration (1% TFA in methylene chloride, room temperature, 0.5h), diphenyl alcohols 6a required more forcing conditions (1% TFA in dichloroethane, reflux, 2h) to effect this conversion.
9. 4), concentrated and purified by silica gel chromatography. Dehydrations were preferably carried out directly on crude alcohols 6 and 6a as described above (ref 8) prior to chromatographic purification.
10. Patch, R. J.; Roberts, J. C.; Gao, H.; Shi, Z.; Gopalsamy, A.; Kongsjahju, A.; Daniels, K.; Kowalczyk, P. J.; van Schravendijk, M-R.; Gordon, K. A.; Pallai, P. V. Bioorg. Med. Chem. Lett. 1996, in press.
11. 3) δ 4.67 (bs, 1 H), 3.37 (s, 2H), 3.13 (m, 2H) 1.50 (m, 2H), 1.43 (s, 9H), 0.90 (s, 6H).
12. 13C-NMR, and mass spectra obtained with the exception of intermediates 4 and 4a, which were not isolated.
13. Mullis, J. C.; Weber, W. P. J Org Chem 1982, 47, 2873.