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Volumn 10, Issue 7, 2008, Pages 743-74

Streamlined process for the esterification and ketalization of shikimic acid en route to the key precursor for oseltamivir phosphate (Tamiflu™)

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EID: 46149122282 PISSN: 14639262 EISSN: 14639270 Source Type: Journal
DOI: 10.1039/b801582a Document Type: Article

Times cited : (22)

References (9)

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- Abrecht, S.¹ Federspiel, M.C.² Estermann, H.³ Fischer, R.⁴ Karpf, M.⁵ Mair, H.-J.⁶ Oberhauser, T.⁷ Rimmler, G.⁸ Trussardi, R.⁹ Zutter, U.¹⁰

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- M. Federspiel R. Fischer M. Hennig H.-J. Mair T. Oberhauser G. Rimmler T. Albiez J. Bruhin H. Estermann C. Gandert V. Göckel S. Götzö U. Hoffmann G. Huber G. Janatsch S. Lauper O. Röckel-Stäbler R. Trussardi A. G. Zwahlen Org. Process Res. Dev. 1999 3 266.
- (1999) Org. Process Res. Dev. , vol.3 , pp. 266
- Federspiel, M.¹ Fischer, R.² Hennig, M.³ Mair, H.-J.⁴ Oberhauser, T.⁵ Rimmler, G.⁶ Albiez, T.⁷ Bruhin, J.⁸ Estermann, H.⁹ Gandert, C.¹⁰ Göckel, V.¹¹ Götzö, S.¹² Hoffmann, U.¹³ Huber, G.¹⁴ Janatsch, G.¹⁵ Lauper, S.¹⁶ Röckel-Stäbler, O.¹⁷ Trussardi, R.¹⁸ Zwahlen, A.G.¹⁹

4
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- WO 2007/074091
- R. Gabel, M. D. Groaning, D. A. Johnston, Epoxide, intermediate in the Tamiflu™ synthesis, WO 2007/074091, July 5, 2007.
- (2007) Epoxide, Intermediate in the Tamiflu™ Synthesis
- Gabel, R.¹ Groaning, M.D.² Johnston, D.A.³

5
- 0037563948
- For a review of the kinetic model used in esterification reactions see
- For a review of the kinetic model used in esterification reactions see: R. Rönnback T. Salmi A. Vuori H. Haario J. Lehtonen A. Sundqvist E. Tirronen Chem. Eng. Sci. 1997 52 3369.
- (1997) Chem. Eng. Sci. , vol.52 , pp. 3369
- Rönnback, R.¹ Salmi, T.² Vuori, A.³ Haario, H.⁴ Lehtonen, J.⁵ Sundqvist, A.⁶ Tirronen, E.⁷

6
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- Initial studies revealed that 3-pentanone was sensitive to acid mediated condensation and polymerization
- Initial studies revealed that 3-pentanone was sensitive to acid mediated condensation and polymerization.

7
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- T. H. Fife L. Hagopian J. Org. Chem. 1966 31 1772.
- (1966) J. Org. Chem. , vol.31 , pp. 1772
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8
- 85032776414
- Method: to a 500 ml round bottomed flask was added triethylorthroformate (96 ml, 574 mmol) followed by 3-pentanone (61 ml, 574 mmol) and ethanol (34 ml, 574 mmol). To this solution was added benzenesulfonic acid (182 mg, 0.2 mol%). The solution was stirred at room temperature for 3 h. This colourless solution is ready for use in the ketalization step
- Method: to a 500 ml round bottomed flask was added triethylorthroformate (96 ml, 574 mmol) followed by 3-pentanone (61 ml, 574 mmol) and ethanol (34 ml, 574 mmol). To this solution was added benzenesulfonic acid (182 mg, 0.2 mol%). The solution was stirred at room temperature for 3 h. This colourless solution is ready for use in the ketalization step.

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