Development of an alternative process for the manufacture of a key starting material for cefovecin sodium

Organic Process Research and Development

Volumn 11, Issue 4, 2007, Pages 742-746

  Norris, Timothy ^a   Nagakura, Isao ^a   Morita, Hiromasa ^a   McLachlan, Grant ^b   Desneves, Joe ^b  

^a PFIZER INC   (United States)

^b Institute of Drug Technology   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547902102     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op700091d     Document Type: Article

References (18)

1. (a) Bateson, J. H.; Burton, G.; Fell, S. C. M. U.S. Patent 6001997, Dec 14, 1999.
2. (b) Bateson, J. H.; Burton, G.; Fell, S. C M. U.S. Patent 6020329, Feb 1, 2000.
3. (c) Bateson, J. H.; Burton, G.; Fell, S. C M. U.S. Patent 6077952, Jun 20, 2000.
4. Cooper R. D. G.; Jose, F. L. J. Am. Chem. Soc. 1970, 92, 2575.
5. (a) Colberg, J. C.; Tucker, J. L.; Zennoni, M.; Giovianni, F.; Donadelli, A. WO 2002046199.
6. (b) Colberg, J. C.; Zennoni, M.; Giovianni, F.; Donadelli, A. WO 2002046198.
7. Bateson, J. H.; Burton, G.; Fell, S. C. M.; Smulders, H. C. J. Antibiot. 1994, 47, 253-256.
8. Boutagy J.; Thomas, R. Chem. Rev. 1974, 1, 87-99.
9. The amount of the phosphate impurity in the reactions with minimal or no excess sodium iodide was initially very low. It was found to increase in the reaction solutions on storage for 24 h at ambient temperature if excess sodium iodide was present. However, 8 solutions may be held at lower temperatures (4°C and -20°C) for up to 4 days.
10. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetradedron Lett. 1984, 25, 2183-2186 and references cited within.
11. DBU and other soluble bases can also be used successfully. The use of hetergeneous bases was not successful.
12. Base causes double bond isomerization.
13. Compound 8 interferes with the KF reagents, and the water content of the reaction solution was unknown. The magnesium sulfate was sufficient to provide a clean reaction.
14. See ref 6.
15. Standard deprotection conditions in cephalosporin chemistry.
16. If the product does not precipitate from the reaction mixture, it decomposes reasonably rapidly.
17. A reference standard of 7 was prepared by coupling of 2 with phenylacetic acid.
18. Monta, H.; Nagakura, I.; Norris, T. WO 2005092900.