An efficient strategy for the synthesis of 1-chloroethyl phosphates and phosphoramidates

Journal of Organic Chemistry

Volumn 70, Issue 22, 2005, Pages 9056-9058

  Kumpulainen, Hanna ^a   Järvinen, Tomi ^a   Saari, Raimo ^a   Lehtonen, Marko ^a   Vepsäläinen, Jouko ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG PRODUCTS; ETHYLENE; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

1-CHLOROETHYL PHOSPHATES; CHLOROPHOSPHATES; HCL GAS; PHOSPHORAMIDATES;

PHOSPHATES;

1 CHLOROETHYL PHOSPHATE; HYDROCHLORIC ACID; PHOSPHATE; PHOSPHORAMIDIC ACID DERIVATIVE; PRODRUG; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

AMIDES; CHLORINE; MOLECULAR STRUCTURE; PHOSPHATES; PHOSPHORIC ACIDS;

EID: 27444440284     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0513562     Document Type: Article

References (23)

1. Fleisher, D.; Bong, R.; Stewart, B. H. Adv. Drug Delivery Res. 1996, 19, 115-130.
2. Chang, S.; Griesgraber, G. W.; Southern, P. J.; Wagner, C. R. J. Med. Chem. 2001, 44, 223-231.
3. Egron, D.; Imbach, J. L.; Gosselin, G.; Aubertin, A. M.; Perigaud, C. J. Med. Chem. 2003, 46, 4564-4571.
4. Freel Meyers, C. L.; Borch, R. F. J. Med. Chem. 2000, 43, 4319-4327.
5. Mathé, C.; Périgaud, C.; Gosselin, G.; Imbach, J.-L. J. Org. Chem. 1998, 63, 8547-8550.
6. Alberg, D. G.; Lauhon, C. T.; Nyfeler, R.; Fassler, A.; Bartlett, P. A. J. Am. Chem. Soc. 1992, 114, 3535-3546.
7. Garrison, A. W.; Boozer, C. E. J. Am. Chem. Soc. 1968, 90, 3486-3494.
8. Krise, J. P.; Zygmunt, J.; Georg, G. I.; Stella, V. J. J. Med. Chem. 1999, 42, 3094-3100.
9. Mantyla, A.; Garnier, T.; Rautio, J.; Nevalainen, T.; Vepsalainen, J.; Koskinen, A.; Croft, S. L.; Jarvinen, T. J. Med. Chem. 2004, 47, 188-195.
10. Ueda, Y.; Matiskella, J. D.; Golik, J.; Connolly, T. P.; Hudyma, T. W.; Venkatesh, S.; Dali, M.; Kang, S. H.; Barbour, N.; Tejwani, R.; Varia, S.; Knipe, J.; Zheng, M.; Mathew, M.; Mosure, K.; Clark, J.; Lamb, L.; Medin, I.; Gao, Q.; Huang, S.; Chen, C. P.; Bronson, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 3669-3672.
11. Slikker, W., Jr.; Andersen, M. E.; Bogdanffy, M. S.; Bus, J. S.; Cohen, S. D.; Conolly, R. B.; David, R. M.; Doerrer, N. G.; Dorman, D. C.; Gaylor, D. W.; Hattis, D.; Rogers, J. M.; Woodrow Setzer, R.; Swenberg, J. A.; Wallace, K. Toxicol. Appl. Pharmacol. 2004, 201, 203-225.
12. Nudelman, A.; Levovich, I.; Cutts, S. M.; Phillips, D. R.; Rephaeli, A. J. Med. Chem. 2005, 48, 1042-1054.
13. Nudelman, A.; Gnizi, E.; Katz, Y.; Azulai, R.; Cohen-Ohana, M.; Zhuk, R.; Sampson, S. R.; Langzam, L.; Fibach, E.; Prus, E.; Pugach, V.; Rephaeli, A. Eur. J. Med. Chem. 2001, 36, 63-74.
14. Alexander, J.; Fromtling, R. A.; Bland, J. A.; Pelak, B. A.; Gilfillan, E. C. J. Med. Chem. 1991, 34, 78-81.
15. Sum, F. W.; Gilbert, A.; Venkatesan, A. M.; Lim, K.; Wong, V.; O'Dell, M.; Francisco, G.; Chen, Z.; Grosu, G.; Baker, J.; Ellingboe, J.; Malamas, M.; Gunawan, I.; Primeau, J.; Largis, E.; Steiner, K. Bioorg. Med. Chem. Lett. 1999, 9, 1921-1926.
16. Bodor, N.; Woods, R.; Raper, C.; Kearney, P.; Kaminski, J. J. J. Med. Chem. 1980, 23, 474-480.
17. Allen, J. F. Chem. Abstr. 1960, 55, 379c.
18. Mark, V.; van Wazer, J. T. J. Org. Chem. 1964, 29, 1006-1008.
19. Steinberg, G. M. J. Org. Chem. 1949, 15, 637-647.
20. Quin, L. D.; Jankowski, S. J. Org. Chem. 1994, 59, 4402-4409.
21. Stowell, J. K.; Widlanski, T. S. J. Am. Chem. Soc. 1994, 116, 789-790.
22. 3h was found to be extremely labile, since it decomposed during warming, column chromatography, and GC-MS/HPLC-MS analysis.
23. Due to their chiral center, OMe signals have different chemical shifts.