A Facile Synthesis of a Sterically Congested Amide: A Convenient Method of Steroidal 17β-Amide Synthesis from 17β-Carboxylic Acid and a Hindered Amine with 2,4,6-Triisopropylbenzenesulfonyl Chloride as a Condensing Reagent

Synlett

Volumn 1996, Issue 6, 1996, Pages 517-518

  Kurata, Hitoshi ^a   Ishibashi, Koki ^a   Kojima, Koichi ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344018450     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5503     Document Type: Article

References (15)

1. Bertz, G. in Comprehensive Organic Synthesis, Trost, B. M.; Winterfeldt, E., Ed, Pergamon Press, Oxford, 1991, vol 6, p381-417.
2. a) Rasmusson, G. H.; Reynolds, G. F.; Steinberg, N. G.; Walton, E.; Patel, G. F.; Liag, T.; Cascieri, M. A.; Cheung, A. H.; Brooks, J R.; Berman, C., J. Med. Chem., 1986, 29, 2298-2315.
3. b) MacGuire, M. A.; Sorenson, E.; Owings, F. W.; Resnick, T. M.; Fox,; Baine, N. H., J. Org. Chem., 1994, 56, 6683-6686.
4. a) Bhattachorya, A.; Williams, J. M.; Amato, J. S.; Dolling, V-H.; Grabowski, E. J. J., Synth. Commun., 1990, 30, 2683-2690.
5. b) Kurata, H.; Ishibashi, K.; Saito, S.; Hamada, T.; Horikoshi, H.; Furukawa, Y.; Kojima, K., Chem. Pharm. Bull., 1996, 44, 115-121.
6. a) Kojima, K.; Kurata, H.; Ishibashi, K.; Horikoshi, H.; Hamada, T., E. P. Patent 484094 (1992) [Chem. Abstr., 1992, 117, 49007f]
7. b) Kojima, K.; Kurata, H.; Horikoshi, H.; Hamada, T., E. P. Patent 567271 (1993)[Chem. Abstr., 1994, 120, 134929].
8. a) Brewster, J. H.; Ciotti, Jr, C. J., J. Am. Chem. Soc., 1955, 77, 6214-6215.
9. b) Mital, A.; Srivastsva, N.; Kumar, A., Indian J. Chem., Sect. B, 1991, 30, 1129-1130.
10. c) Corey, E. J.; Weigel, L. O.; Floyd, D.; Bock, M. G., J. Am. Chem. Soc., 1978, 100, 2916-2918.
11. Lindberg, U. H.; Jakupovic, E.; Yylen, B.; Ulff, B., Acta Pharm. Suecica, 1970, 7, 531-542.
12. 3, ppm): 0.68 (3H, s), 0.90 (3H, s), 1.69 (3H, s), 1.71 (3H, s), 3.08 (1H, dd, J=4, 13Hz), 3.80 (3H, s), 5.49 (1H, brs), 6.25 (1H, brs), 6.88 (2H, d, J=9Hz), 7.30 (2H, d, J=9Hz).
13. Rasmusson, G. H.; Tolman, R. L.; Patel, G. F, E. P. patent 465141 (1991)) [Chem. Abstr., 1992, 116, 152151].
14. Baldeman, D.; Kalir, A., Synthesis, 1978, 1978, 24-25.
15. 3, ppm): 0.73 (3H, s), 0.97 (3H, s), 1.68 (3H, s), 1.70 (3H, s), 2.36 (1H, dd, J=5, 18Hz), 2.56 (1H, m), 3.79 (6H, s), 5.53 (1H, m), 5.57 (1H, brs), 5.99 (1H, s), 6.34 (1H, t, J=2Hz), 6.56 (2H, d, J=2Hz).