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Florfenicol

Florfenicol 12 [1-2] (marketed by Schering-Plough Animal Health under the trade name Nuflor) is a fluorinated synthetic analog of thiamphenicol [3].
In the United States, florfenicol is currently indicated for the treatment of bovine respiratory disease (BRD) associated with Mannheimia (Pasteurella) haemolytica, Pasteurella multocida, and Haemophilus somnus, for treatment of bovine interdigital phlegmon (foot rot, acute interdigital necrobacillosis, infectious pododermatitis) associated with Fusobacterium necrophorum and Bacteroides melaninogenicus.

Synthesis

A number of synthetic routes to florfenicol utilizing different strategies to construct its two stereocentres have been developed [2,4-12]. The synthetic strategy developed by the Schering–Plough company in 1990, via (1R,2R)-2-amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol 10 (Scheme1), is a reliable approach toward florfenicol on an industrial scale [10-11]. A chemo-enzymatic methodology  to prepare 10 involved the hydrocyanation of 4-methylthiobenzaldehyde catalyzed by (R)-hydroxynitrile lyase [12]. An efficient approach for the enantioselective synthesis of florfenicol by using a vanadium-catalyzed asymmetric epoxidation as a key step has recently been reported  (see scheme 1) [13].

 

Scheme 1. Asymmetric synthesis of florfenicol

 

 


Medicinal Chemistry

CAS number: 0076639-94-6   EINECS:

Molecular Formula: C12H14Cl2FNO4S

Average mass: 358.21 Da
Monoisotopic mass:

Systematic name: 2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
SMILES: ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CF

Std. InChI: 1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1

Properties
Melting Point:  

 

 

 

 


1. Nagabhushan, T. L. Eur Pat Appl. EP14437 A2, 1980.

2. Jommi, G.; Pagliarin, R.; Chiarino, D.; Fantucci, M. Gazz. Chim. Ital. 115, 653–658, 1985.

3. Syriopoulou VP, Harding AL, Goldmann DA, Smith AL. "In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol." Antimicrob. Agents Chemother. 19, (2): 294–7, 1981.

4. Jommi, G.; Pagliarin, R.; Tavecchia, P.; Chiarino, D.; Fantucci, M. Gazz. Chim. Ital. 116, 485–489, 1986.

5. Jommi, G.; Ripa, A.; Ripa, G.; Sisti, M. Gazz. Chim. Ital. 118, 75–76, 1988.

6. Jommi, G.; Chiarino, D. Pagliarin, R. Eur Pat Appl. EP677511 A2, 1995.

7. Tyson, R. Chem. Ind. 118–122, 1988.

8. Schumacher, D. P.; Clark, J. E.; Murphy, B. F.; Fischer, P. A. J. Org. Chem. 55, 5291–5294, 1990.

9. Clark, J. E.; Fischer, P. A.; Schumacher, D. P. Synthesis 10, 891–894, 1991.

10. Wu, G. Z.; Tormos, W. I. PCT Int. Appl. WO 9414764 A1, 1994.

11. Wu, G. Z.; Schumacher, D. P.; Tormos, W.; Clark, J. E.; Murphy, B. L. J. Org. Chem. 62, 2996–2998, 1997.

12. Lu, W. Y.; Chen, P. R.; Lin, G. Q. Tetrahedron 64, 7822–7827, 2008.

13. Feng Li, Zhong-Hua Wang, Lei Zhao, Fang-Jun Xiong, Qiu-Qin He, Fen-Er Chen. "An efficient enantioselective synthesis of florfenicol
via a vanadium-catalyzed asymmetric epoxidation". Tetrahedron: Asymmetry 22, 1337–1341, 2011.


 

 

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