Single-Step Preparation of 1-Hydroxybisphosphonates via Addition of Dialkyl Phosphite Potassium Anions to Acid Chlorides

Journal of Organic Chemistry

Volumn 60, Issue 16, 1995, Pages 5209-5213

  Ruel, Réjean ^a   Bouvier, Jean Pierre ^a   Young, Robert N ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BISPHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

EID: 0029084326     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00121a044     Document Type: Article

References (31)

1. Fleisch, H. In Handbook of Experimental Pharmacology, Mundy, G. R., Martin, T. J., Eds.; Springer-Verlag: Berlin, Heidelberg, 1993; pp 377-418.
2. Raisz, L. G. N. Engl. J. Med. 1988, 318, 818-828.
3. Jung, A.; Bisaz, S.; Fleisch, H. Calc. Tiss. Res. 1973, 11, 269-280.
4. Sahni, M.; Guenther, H. L.; Fleisch, H.; Collin, P.; Martin, T. J. J. Clin. Invest. 1993, 91 (5), 2004-2011.
5. Nicholson, D. A.; Cilley, W. A. J. Org. Chem. 1970, 35, 3149-3150.
6. Teulade, M.-P.; Savignac, P. J. Organomet. Chem. 1986, 304, 283-300.
7. Degenhardt, C. R.; Burdsall, D. C. J. Org. Chem. 1986, 51, 3488-3490.
8. Takeuchi, M.; Sakamoto, S.; Yoshida, M.; Abe, T.; Isomura, Y. Chem. Pharm. Bull. 1993, 41 (A), 688-693.
9. Sturtz, G.; Guervenou, J. Synthesis 1991, 661-662 and references therein.
10. Hutchinson, D. W.; Thornton, D. M. J. Organomet. Chem. 1988, 346, 341-348.
11. Jouko, V.; Heikki, N.; Esko, P. J. Labelled Cmpds Radiopharm. 1991, 29 (11), 1191-1196.
12. Neidlein, R.; Eichinger, T. Synthesis 1991, 1228-1230.
13. Vepsäläinen, J.; Nupponen, H.; Pohjala, E.; Ahlgren, M.; Vainiotalo, P. J. Chem. Soc., Perkin Trans. 2 1992, 835-842.
14. Nicholson, D. A.; Vaughn, H. J. Org. Chem. 1971, 36, 3843-3845.
15. Nguyen, L. M.; Niesor, E.; Bentzen, C. L. J. Med. Chem. 1987, 30, 1426-1433.
16. Kaas, S. M.; Ebetino, F. H.; Francis, M. D. WO 93/24496 1993 and references therein.
17. Bauss, F.; Mühlbauer, R. C. Drugs Future 1994, 19 (1), 13.
18. Jaeggi, K. A.; Widler, L. U. S. patent 4, 939, 130, 1990.
19. McConnell, R. L.; Coover, H. W., Jr. J. Am. Chem. Soc. 1956, 78, 4450-4452.
20. Arbuzow, B. A. Pure Appl. Chem. 1964, 9, 307-335.
21. Bhattacharya, A. K.; Thyagaijan, G. Chem. Rev. 1981, 81, 415-430.
22. Tam, C. C.; Mattocks, K. L.; Tishler, M. Proc. Natl Acad. Sci. U. SA. 1981, 78, 3301-3304.
23. Fitch, S. J.; Moedritzer, K. J. Am. Chem. Soc. 1962, 84, 1876-1879.
24. Ishihara, T.; Maekawa, T.; Yamasaki, Y.; Ando. J. Fluorine Chem. 1986, 34 (5), 271-274.
25. Ishihara, T.; Maekawa, T.; Yamasaki, Y.; Ando. Tetrahedron Lett. 1983, 24, 4229-4232.
26. Breuer, E.; Karaman, R.; Goldblum, A. Phosphorus Sulfur 1984, 21, 119-120.
27. Pashinkin, A. P.; Gazizov, T. K.; Pudovik, A. N. Zh. Obshch. Khim. 1970, 40, 28.
28. Pashinkin, A. P.; Gazizov, T. K.; Pudovik, A. N. Chem. Abstr. 1970, 72, 100827.
29. Terauchi, K.; Sakurai, H. Bull. Chem. Soc. Jpn. 1970, 43, 883-890.
30. Sekine, M.; Satoh, M.; Yamagata, H.; Hata, T. J. Org. Chem. 1980, 45, 4162-4167.
31. Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617-3620.