Synthesis of 2-trifluoromethyl-1,3-oxazolidines as hydrolytically stable pseudoprolines

Journal of Organic Chemistry

Volumn 75, Issue 12, 2010, Pages 4135-4145

  Chaume, Grégory ^a   Barbeau, Olivier ^a   Lesot, Philippe ^b   Brigaud, Thierry ^a  

^a Université Paris Seine   (France)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDIFICATION; CONFIGURATIONALLY; HEMIACETALS; OXAZOLIDINES; TRIFLUOROACETALDEHYDE; TRIFLUOROMETHYL; TRIFLUOROMETHYL GROUP;

ACETONE; AMINO ACIDS; ESTERS;

PHOSPHATASES;

2 TRIFLUOROMETHYL 1,3 OXAZOLIDINE DERIVATIVE; ACETALDEHYDE; ACETONE; ESTER DERIVATIVE; N ACETYL 2 TRIFLUOROMETHYL 2 METHYLOXAZOLIDINE 4 CARBOXYLIC ACID METHYL ESTER; N ACETYL 2 TRIFLUOROMETHYLOXAZOLIDINE 4 CARBOXYLIC ACID METHYL ESTER; N ACETYL 2 TRIFLUOROMETHYLOXAZOLIDINE 4 N METHYLAMIDE; N PROPIONYL 2 TRIFLUOROMETHYLOXAZOLIDINE 4 CARBOXYLIC ACID METHYL ESTER; OXAZOLIDINE DERIVATIVE; PROLINE DERIVATIVE; SERINE ESTER DERIVATIVE; TRIFLUOROACETALDEHYDE HEMIACETAL; TRIFLUOROACETONE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CIS TRANS ISOMERISM; NONHUMAN; POLYMERIZATION; SYNTHESIS;

ACYLATION; ESTERS; FLUORINE; METHANE; MOLECULAR STRUCTURE; OXAZOLES; PROLINE; THIAZOLES;

EID: 77953491258     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100518t     Document Type: Article

References (72)

1. Moroder, L.; Renner, C.; Lopez, J. J.; Mutter, M.; Tuchscherer, G. In Cis-trans Isomerization in Biochemistry; Dugave, C., Ed; Wiley-VCH: Weinheim, 2006; pp 225 - 259.
2. Karoyan, P.; Sagan, S.; Lequin, O.; Quancard, J.; Lavielle, S.; Chassaing, G. Targets Heterocycl. Syst. 2004, 8, 216-273
3. van Esseveldt, B. C. J.; Vervoort, P. W. H.; van Delft, F. L.; Rutjes, F. P. J. T. J. Org. Chem. 2005, 70, 1791-1795 and references therein.
4. Jenkins, C. L.; Lin, G.; Duo, J.; Rapolu, D.; Guzei, I. A.; Raines, R. T.; Krow, G. R. J. Org. Chem. 2004, 69, 8565-8573 and references therein.
5. Del Valle, J. R.; Goodman, M. J. Org. Chem. 2003, 68, 3923-3931 and references therein.
6. Bernardi, F.; Garavelli, M.; Scatizzi, M.; Tomasini., C.; Trigari, V.; Crisma, M.; Formaggio, F.; Peggion, C.; Toniolo, C. Chem. - Eur. J. 2002, 8, 2516-2525
7. Tomasini, C.; Villa, M. Tetrahedron Lett. 2001, 42, 5211-5214
8. Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wöhr, T.; Mutter, M. J. Am. Chem. Soc. 1997, 119, 918-925
9. Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714-2720
10. Sager, C.; Mutter, M.; Dumy, P. Tetrahedron Lett. 1999, 40, 7987-7991
11. Ruckle, T.; de Lavallaz, P.; Keller, M.; Dumy, P.; Mutter, M. Tetrahedron 1999, 55, 11281-11288
12. Skropeta, D.; Jolliffe, K. A.; Turner, P. J. Org. Chem. 2004, 69, 8804-8809
13. Sayyadi, N.; Skropeta, D.; Jolliffe, K. A. Org. Lett. 2005, 7, 5497-5499
14. Wöhr, T.; Wahl, F.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X.; Mutter, M. J. Am. Chem. Soc. 1996, 118, 9218-9227
15. Haack, T.; Mutter, M. Tetrahedron Lett. 1992, 33, 1589-1592
16. Keller, M.; Wöhr, T.; Dumy, P.; Patiny, L.; Mutter, M. Chem. - Eur. J. 2002, 8, 2516-2525
17. Wittelsberger, A.; Keller, M.; Scarpellino, L.; Patiny, L.; Acha-Orbea, H.; Mutter, M. Angew. Chem., Int. Ed. 2000, 39, 1111-1115
18. Keller, M.; Boissard, C.; Patiny, L.; Chung, N. N.; Lemieux, C.; Mutter, M.; Schiller, P. W. J. Med. Chem. 2001, 44, 3896-3903
19. Tuchscherer, G.; Grell, D.; Tatsu, Y.; Durieux, P.; Fernandez-Carneado, J.; Hengst, B.; Kardinal, C.; Feller, S. Angew. Chem., Int. Ed. 2001, 40, 2844-2848
20. Wittelsberger, A.; Patiny, L.; Slaninova, J.; Barberis, C.; Mutter, M. J. Med. Chem. 2005, 48, 6553-6562
21. Patiny, L.; Guichou, J.-F.; Keller, M.; Turpin, O.; Ruckle, T.; Lhote, P.; Buetler, T. M.; Ruegg, U. T.; Wenger, R. M.; Mutter, M. Tetrahedron 2003, 59, 5241-5249
22. Jamet, H.; Jourdan, M.; Dumy, P. J. Phys. Chem. B 2008, 112, 9975-9981 and references therein.
23. Begue, J.-P.; Bonnet-Delpon, D., Eds. Bioorganic and Medicinal Chemistry of Fluorine; Wiley: New York, 2008.
24. Ojima, I., Ed. Fluorine In Medicinal Chemistry And Chemical Biology; Wiley-Blackwell: New York, 2009.
25. Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; American Chemical Society: Washington, DC, 1996.
26. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004.
27. Smart, B. E. J. Fluorine Chem. 2001, 109, 3-11
28. OHagan, D. Chem. Soc. Rev. 2008, 37, 308-319
29. OHagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652
30. Uneyama, K., Ed. Organofluorine Chemistry; Blackwell Publishing: Oxford, 2006.
31. Soloshonok, V. A., Ed. Fluorine-Containing Synthons; American Chemical Society: Washington, DC, 2005; Vol. 911.
32. The size of a trifluoromethyl group is evaluated to be intermediate between an isopropyl and an ethyl group. Leroux, F. ChemBioChem 2004, 5, 644-649
33. Beausoleil, E.; Lubell, W. D. J. Am. Chem. Soc. 1996, 118, 12902-12908
34. Uneyama, K. In Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; John Wiley & Sons Ltd.: Chichester, UK, 2009; 213 - 256.
35. Kukhar, V. P.; Soloshonok, V. A. In Fluorine Containing Amino Acids: Synthesis and Properties; Wiley: New York, 1995.
36. Zanda, M. New J. Chem. 2004, 28, 1401-1411 and references cited therein
37. Molteni, M.; Pesenti, C.; Sani, M.; Volonterio, A.; Zanda, M. J. Fluorine Chem. 2004, 125, 1335-1743 and references cited therein
38. Barth, D.; Milbradt, A. G.; Renner, C.; Moroder, L. ChemBioChem 2004, 5, 79-86
39. Smits, R.; Cadicamo, C. D.; Burger, K.; Koksch, B. Chem. Soc. Rev. 2008, 37, 1727-1739 and references therein.
40. Koksch, B.; Sewald, N.; Hofmann, H.-J.; Burger, K.; Jakubke, H.-D. J. Pept. Sci. 1997, 3, 157-167
41. Jaeckel, C.; Koksch, B. Eur. J. Org. Chem. 2005, 4483-4503
42. Yoder, N. C.; Kumar, K. Chem. Soc. Rev. 2002, 31, 335-341
43. Meng, H.; Kumar, K. J. Am. Chem. Soc. 2007, 129, 15615-15622
44. Molteni, M.; Pesenti, C.; Sani, M.; Volonterio, A.; Zanda, M. J. Fluorine Chem. 2004, 125, 1335-1743
45. Zanda, M. New J. Chem. 2004, 28, 1401-1411
46. Mykhailiuk, P. K.; Afonin, S.; Palamarchuk, G. V.; Shishkin, O. V.; Ulrich, A. S.; Komarov, I. V. Angew. Chem., Int. Ed. 2008, 47, 5765-5767
47. Mikhailiuk, P. K.; Afonin, S.; Chernega, A. N.; Rusanov, E. B.; Platonov, M. O.; Dubinina, G. G.; Berditsch, M.; Ulrich, A. S.; Komarov, I. V. Angew. Chem., Int. Ed. 2006, 45, 5659-5661
48. Maisch, D.; Wadhwani, P.; Afonin, S.; Bottcher, C.; Koksch, B.; Ulrich, A. S. J. Am. Chem. Soc. 2009, 131, 15596-15597
49. Jackson, J. C.; Hammill, J. T.; Mehl, R. A. J. Am. Chem. Soc. 2007, 129, 1160-1166
50. Keller, M.; Lehmann, C.; Mutter, M. Tetrahedron 1999, 55, 413-422
51. Woehr, T.; Mutter, M. Tetrahedron Lett. 1995, 36, 3847-3848
52. Haack, T.; Mutter, M. Tetrahedron Lett. 1992, 33, 1589-1592
53. Seebach, D.; Sommerfeld, T. L.; Jiang, Q.; Venanzi, L. M. Helv. Chim. Acta 1994, 77, 1313-1330
54. Anwar, M.; Moloney, M. G. Tetrahedron Lett. 2007, 48, 7259-7262
55. Guichou, J.-F.; Patiny, L.; Mutter, M. Tetrahedron Lett. 2002, 43, 4389-4390
56. Selambarom, J.; Smadjaa, J.; Pavia, A. A. Tetrahedron Lett. 2005, 46, 615-617
57. Selambarom, J.; Smadja, J.; Thomas, O.; Parrot, I.; Martinez, J.; Pavia, A. A. Int. J. Pept. Res. Ther. 2005, 11, 267-270
58. Chaume, G.; VanSeveren, M.-C.; Ricard, L.; Brigaud, T. J. Fluorine Chem. 2008, 129, 1104-1109
59. Caupène, C.; Chaume, G.; Ricard, L.; Brigaud, T. Org. Lett. 2009, 11, 209-212
60. f values differences.
61. HyperChem is a registered trademark of Hypercube, Inc.
62. The absolute configurations of 3 and 4 could not be assigned.
63. Schlosser, M. Angew. Chem., Int. Ed. 1998, 110, 1496-1513
64. For examples of peptides coupling at the N -terminal position of α-Tfm-amino acids, see: Koksch, B.; Quaedflieg, P. J. L. M.; Michel, T.; Burger, K.; Broxterman, Q. B.; Schoemaker, H. E. Tetrahedron: Asymmetry 2004, 15, 1401-1407
65. Dal Pozzo, A.; Ni, M.; Muzi, L.; Caporale, A.; de Castiglione, R.; Kaptein, B.; Broxterman, Q. B.; Formaggio, F. J. Org. Chem. 2002, 67, 6372-6375
66. Chaume, G.; Lensen, N.; Caupene, C.; Brigaud, T. Eur. J. Org. Chem. 2009, 5717-5724
67. Philippe, C.; Milcent, T.; Nguyen Thi Ngoc, T.; Crousse, B.; Bonnet-Delpon, D. Eur. J. Org. Chem. 2009, 71, 5215-5223
68. Varala, R.; Nuvula, S.; Adapa, S. R. J. Org. Chem. 2006, 71, 8283-8286
69. Ando, W.; Igarashi, Y.; Huang, L. Chem. Lett. 1987, 1361-1364
70. Dal Pozzo, A.; Bergonzi, R.; Ni, M. Tetrahedron Lett. 2001, 42, 3925-3927
71. Dal Pozzo, A.; Ni, M.; Muzi, L.; Caporale, A.; de Castiglione, R.; Kaptein, B.; Broxterman, Q. B.; Formaggio, F. J. Org. Chem. 2002, 67, 6372-6375
72. Cis / trans amide isomers were discriminated from possible diastereomers or side products by coalescence of NMR signals at higher temperature.