A convenient and practical method for N-acylation of 2 oxazolidinone chiral auxiliaries with acids

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9369-9372

  Prashad, Mahavir ^a   Kim, Hong Yong ^a   Har, Denis ^a   Repic, Oljan ^a   Blacklock, Thomas J ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL BINDING; CHIRALITY; DRUG SYNTHESIS;

EID: 0032542166     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02112-1     Document Type: Article

References (18)

1. 1. Evans, D. A. Aldrichimica Acta 1982, 15, 23-32.
2. 2. Ager, J. A.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997, 30, 3-12.
3. 3. Ager, J. A.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
4. 4. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
5. 5. Evans, D. A.; Bartoli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
6. 6. Evans, D. A.; Ennis, M. D.; Le, T. J. Am. Chem. Soc. 1984, 106, 1154-1156.
7. 7. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
8. 8. Azam, S.; D'Souza, A. A.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1996, 621-627.
9. 9. Evans, D. A.; Ellman J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
10. 10. Ho, G. J.; Mathre, D. J. J. Org. Chem. 1995, 60, 2271-2273.
11. 11. Ager, D. J.; Allen, D. R.; Schaad, D. R. Synthesis 1996, 1283-1285.
12. 12. Lee, J. Y.; Chung, Y. J.; Kim, B. H. Synlett 1994, 197-198.
13. 13. Thom, C.; Kocienski, P. Synthesis 1992, 582-586.
14. 14. Decomposition of N-acylated-2-oxazolidinones under basic conditions via a ketene pathway is aslo known. Hoekstra, M. S.; Sobieray, D. M.; Schwindt, M. A.; Mulhern, T. A.; Grote, T. M.; Huckabee, B. K.; Hendrickson, V. S.; Franklin, L. C.; Granger, E. J.; Karrick, G. L. Org. Proc. Res. Dev. 1997, 1, 26-38.
15. 15. Knol, J.; Feringa, B. L. Synth. Commun. 1996, 26, 261-268.
16. 16. Typical procedure (Table 1): To a mixture of 2-oxazolidinone chiral auxiliary (1 eq.), acid (2 eq.) in toluene (1.6 mL / mmol) was added triethylamine (4 eq.). The mixture was heated to an internal temperature of 80 °C to obtain a solution. To the reaction mixture was added a solution of pivaloyl chloride (2 eq.) in toluene (0.2 mL / mmol) at a rate to maintain an internal temperature of 80 °C. The mixture was then heated to an internal temperature of 110 °C and stirred at this temperature for 14 h (overnight). The reaction mixture was cooled to room temperature and was washed with 2 N hydrochloric acid, 5% aqueous sodium carbonate, and brine. The organic layer was concentrated and the crude product was purified by silica gel chromatography.
17. 17. All the compounds gave satisfactory spectral data.
18. 18. Procedure (Table 2) : To a mixture of 2-oxazolidinone chiral auxiliary (1 eq.), arylacetic acid (1.14 eq.) in toluene (1.6 mL / mmol) was added triethylamine (3 eq.). The mixture was heated to an internal temperature of 80 °C to obtain a solution. To the reaction mixture was added pivaloyl chloride (1.19 eq.) in toluene (0.2 mL / mmol) at a rate to maintain an internal temperature of 80 °C. The mixture was stirred at 80 °C (or 110 °C; Table 2) for 2 h and additional pivaloyl chloride (0.6 eq.) was added while maintaining the internal temperature at 80 °C (or 110 °C). The mixture was stirred for an additional 3 h at 80 °C (or 110 °C). The reaction mixture was cooled to room temperature and was washed with 2 N hydrochloric acid, 5% aqueous sodium carbonate, and brine. The organic layer was concentrated and the crude product was purified by silica gel chromatography.