Controlled racemization and asymmetric transformation of α-substituted carboxylic acids in the melt

Tetrahedron Asymmetry

Volumn 10, Issue 19, 1999, Pages 3701-3718

  Ebbers, Eelco J ^a,c   Ariaans, Gerry J A ^a   Bruggink, Alle ^a,b,d   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b Chemferm   (Netherlands)

^c Mercachem BV   (Netherlands)

^d DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; HYDRATROPIC ACID; IBUPROFEN; MANDELIC ACID; NAPROXEN; SCHIFF BASE; SOLVENT;

ARTICLE; CATALYSIS; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE;

EID: 0033429256     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00387-0     Document Type: Article

References (64)

1. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; John Wiley & Sons: New York, 1981; Chapter 6.
2. (a) Yamada, S.; Hongo, C.; Yoshioka, R.; Chibata, I. J. Org. Chem. 1983, 48, 843.
3. (b) Hongo, C.; Yoshioka, R.; Tohyama, M.; Yamada, S.; Chibata, I. Bull. Chem. Soc. Jpn. 1983, 56, 3744.
4. (c) Yoshioka, R.; Ohtsuki, O.; Senuma, M.; Tosa, T. Chem. Pharm. Bull. 1989, 37, 883.
5. (d) Bhattacharya, A.; Araullo-McAdams, C.; Meier, M. B. Synth. Commun. 1994, 2449.
6. (e) Yoshioka, R.; Tohyama, M.; Ohtsuki, O.; Yamada, S.; Chibata, I. Bull. Chem. Soc. Jpn. 1987, 60, 649, 4321.
7. (f) Hongo, C.; Tohyama, M.; Yoshioka, R.; Yamada, S.; Chibata, I. Bull. Chem. Soc. Jpn. 1985, 58, 433.
8. (g) Shiraiwa, T.; Sjinjo, K.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1991, 64, 3251, 3741.
9. (h) Miyzaki, H.; Ohta, A.; Kawakatsu, N.; Waki, Y.; Gogun, Y.; Shiraiwa, T.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1993, 66, 536.
10. Ebbers, E. J.; Ariaans, G. J. A.; Houbiers, J. P. M.; Bruggink, A.; Zwanenburg, B. Tetrahedron 1997, 53, 9417-9476.
11. (a) DE 2838882, 790315 (770906), American Cyanamid Co., USA, 1979; Chem. Abstr. 1979, 90, 203672.
12. (b) US Patent 4259521, 810331 (791009), American Cyanamid Co., USA, 1981; Chem. Abstr. 1981, 95, 6842.
13. (c) Campbell, A. N.; Campbell, A. J. R. J. Am. Chem. Soc. 1932, 54, 4581.
14. (d) Winther, C. Phys. Chem. 56, 540.
15. (e) Kresge, A. J. Pure Appl. Chem. 1991, 63, 213.
16. (f) Chiang, Y.; Kresge, A. J.; Praszynsky, P.; Schepp, N. P.; Wirz, J. Angew. Chem. 1990, 102, 810.
17. Racemization by treatment of talc: Akekawa, A.; Hayakawa, S. Bull. Chem. Soc. Jpn. 1987, 60, 19.
18. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
19. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
20. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
21. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
22. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
23. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
24. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
25. Racemization by treatment of racemate: (a) Kenyon, G. L.; Hegeman, G. D. Adv. Enzymol. 1979, 50, 325. (b) Gerlt, J. A.; Kozarich, J. W. J. Am. Chem. Soc. 1991, 113, 9667. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928. (d) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552. (e) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569. (f) Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178. (g) Babbitt, P. C.; Mrachko, G. T.; Hasson, M. S.; Huisman, G. W.; Kolter, R.; Ringe, D.; Petsko, G. A.; Kenyon, G. L. Science 1995, 267, 1159. (h) Westheimer, F. H. Tetrahedron 1995, 51, 3.
26. 2O=10:30:3 at 150°C in dimethyl sulfoxide. Under the same conditions mandelic acid was racemized accompanied by oxidation to benzoic acid.
27. Ethyl mandelate racemized quantitatively under Oppenauer oxidation conditions. However, it was proven that racemization was induced by the base catalyst instead of the oxidation mechanism. Mandelic acid did not racemize under these conditions.
28. (a) Cram, D. J.; Rickborn; Kingsbury, C. A.; Haberfield, P. J. Am. Chem. Soc. 1961, 83, 3678.
29. (b) Cram, D. J.; Gosser J. Am. Chem. Soc. 1963, 85, 3890; idem J. Am. Chem. Soc. 1964, 86, 5457.
30. (b) Cram, D. J.; Gosser J. Am. Chem. Soc. 1963, 85, 3890; idem J. Am. Chem. Soc. 1964, 86, 5457.
31. (c) Roitman, Cram, D. J. J. Am. Chem. Soc. 1971, 93, 2225.
32. Data obtained from Beilstein's Handbook of Organic Chemistry; Springer Verlag: New York, 1986; 4th ed., Parts I-IV.
33. Schwesinger, R. Chimia 1985, 39, 269.
34. Steward, J. J. P. MOPAC 93 Manual; Fujitsu Limited, 1993
35. Ebbers, E. J.; Ariaans, G. J. A.; Bruggink, A.; Zwanenburg, B. In preparation.
36. (a) Kozma, D.; Pokol, G.; Acs, M. J. Chem. Soc., Perkin Trans. 2 1992, 435.
37. (b) Stoll, A.; Preyer, J.; Hofmann, A. Helv. Chim. Acta 1943, 26, 929.
38. (c) Acs, M.; Novotny-Bregger, E.; Simon, K.; Argay, G. J. Chem. Soc., Perkin Trans. 2 1992, 2011.
39. (d) Kozma, D.; Nyeki, A.; Acs, M.; Fogassy, E. Tetrahedron: Asymmetry 1994, 5, 315.
40. (e) Bergman, S. Arkiv Kemi, 1926, 9, 1.
41. (f) Jarowski, C.; Hartung, W. H. J. Org. Chem. 1947, 8, 564.
42. (g) Skita, A.; Keil, F.; Meiner, H. Berichte 1933, 974.
43. (h) Kazan, J.; Chen, S. US Patent 4259521, 31-03-81 (09-10-79), Am. Cyanamid, USA, 1981; Chem. Abstr. 1981, 95, 6842.
44. Ebbers, E. J.; Plum, B. J. M.; Ariaans, G. J. A.; Kaptein, B.; Broxterman, Q. B.; Bruggink, A.; Zwanenburg, B. Tetrahedron: Asymmetry 1997, 8, 4047.
45. (a) Pettersson, K. Arkiv Kemi 1956, 10, 283.
46. (b) Leclerq, M.; Jacques, J. Bull. Soc. Chim. Fr. 1975, 2052.
47. (a) Manimaran, T.; Impastato, F. J. US Patent 5015764, Ethyl Corp., USA, 18-06-90, 1991; Chem. Abstr. 1991, 115, 135162.
48. (b) Nicholson, J. S.; Tantum, J. G. US Patent 4209638, 1980.
49. (c) Lukas, H.; Schuster, O.; Rau, G. US Patent 4983765, 1991.
50. (d) WO 9315039, Ethyl Corp., USA, 18-12-92, 1993; Chem. Abstr. 1993, 119, 270637.
51. (a) Tung, H.; Waterson, S.; Reynolds, S. US Patent 4994604, Merck, 10-01-90.
52. (b) Bhattacharya, A.; Fritch, J. R.; Murphy, C. D.; Zeugler, L. D.; McAdams, C. A. US Patent 5380867, Hoechst, 19-10-93.
53. Roger, R.; Neilson, D. G. J. Chem. Soc. 1960, 627.
54. Kozma, D.; Acs, M.; Fogassy, E. Tetrahedron 1994, 50, 6907.
55. (b) EP Patent 0132854, Blaschim S.p.A., 19-04-84, 1985; Chem. Abstr. 1985, 103, 6055
56. Felder, E.; Pitre, D.; Zutter, H. EP Patent 0007116, Syntex, 17-07-79.
57. US Patent 3904683, Syntex, 09-09-75, Chem. Abstr. 83, 206011.
58. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
59. Manimaran, T.; Stahly, G. P. Tetrahedron: Asymmetry 1993, 4, 1949.
60. Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384.
61. McKenzie, A.; Smith, I. A. J. Chem. Soc. 121, 1353.
62. Kirby, G. W.; Nazeer, M. Tetrahedron Lett. 1988, 29, 6173.
63. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109.
64. Sen, S. E.; Anliker, K. S. J. Chem. Educ. 1996, 73, 569.