Phosgenated p-Nitrophenyl(polystyrene)ketoxime or Phoxime Resin. A New Resin for the Solid-Phase Synthesis of Ureas via Thermolytic Cleavage of Oxime-Carbamates

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4802-4807

  Scialdone, Mark A ^a   Shuey, Steven W ^a   Soper, Paul ^a   Hamuro, Yoshitomo ^a   Burns, David M ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000631409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9716542     Document Type: Article

References (50)

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8. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
9. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
10. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
11. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
12. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
13. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
14. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
15. Other isocyanate equivalents in urea synthesis. Use of p-nitrophenyl carbamates, see: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055-4058. (b) Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312. (c) Choy, N.; Moon, K. Y.; Park, C.; Son, Y. C.; Jung, W. H.; Choi, H.; Lee, C. S.; Kim, C. R.; Kim, S. C.; Yoon, H. Org. Prep. Proc. 1996, 28, 173-177. (d) Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338. Use of di-tert-butyl dicarbonate, see: (e) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497-2500. (f) Knolker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502-504. (g) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507-508. Use of S,S-dimethyl dithiocarbonate, see: (h) Leung, M.-k.; Lai, J.-L.; Lau, K.-H.; Yu, H.-h.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175-4179.
16. Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240-1245.
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22. For use of commercially available p-nitrophenyl carbonate resin from Novabiochem (Catal. No. 01-64-0131) as the phosgene equivalent in hydantoin library synthesis, see: Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937-940. Two similar active carbonate resins have been recently been reported; see: Alsina, J.; Chiva, C.; Ortiz, M.; Rabanal, F.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 883-886 and Cuny, G. D.; Cao, J.; Hauske, J. R.Tetrahedron Lett. 1997, 38, 5237-5240.
23. For use of commercially available p-nitrophenyl carbonate resin from Novabiochem (Catal. No. 01-64-0131) as the phosgene equivalent in hydantoin library synthesis, see: Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937-940. Two similar active carbonate resins have been recently been reported; see: Alsina, J.; Chiva, C.; Ortiz, M.; Rabanal, F.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 883-886 and Cuny, G. D.; Cao, J.; Hauske, J. R.Tetrahedron Lett. 1997, 38, 5237-5240.
24. For use of commercially available p-nitrophenyl carbonate resin from Novabiochem (Catal. No. 01-64-0131) as the phosgene equivalent in hydantoin library synthesis, see: Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937-940. Two similar active carbonate resins have been recently been reported; see: Alsina, J.; Chiva, C.; Ortiz, M.; Rabanal, F.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 883-886 and Cuny, G. D.; Cao, J.; Hauske, J. R.Tetrahedron Lett. 1997, 38, 5237-5240.
25. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5835-5838.
26. Kim, S. W.; Ahn, S. Y.; Koh, J. S.; Lee, J. H.; Ro, S.; Cho, H. Y. Tetrahedron Lett. 1997, 38, 4603-4606.
27. Buckmann, B.; Mohan, R. Tetrahedron Lett. 1996, 37, 4439-4442.
28. Gouilleux, L.; Fehrentz, J.-A.; Winternitz, F.; Martinez, J. Tetrahedron Lett. 1996, 37, 7031.
29. Smith, A. L.; Thompson, C. G.; Leeson, P. D. Bioorg. Med. Chem. Lett. 1996, 6, 1483-1486.
30. Wicks, Z. W. Prog. Org. Coat. 1975, 3, 73-99.
31. Wicks, Z. W. Prog. Org. Coat. 1981, 9, 3-28.
32. DeGrado, W. F.; Kaiser, E. T. J. Org. Chem. 1980, 45, 1295-1300.
33. DeGrado, W. F.; Kaiser, E. T. J. Org. Chem. 1982, 47, 3258-3261.
34. Scialdone, M. A. Tetrahedron Lett. 1996, 37, 8141-8144.
35. For other recent reports of thermolytic cleavage off a polymer support, see refs 14, 18, 19, and: (a) Kolodziej, A. A.; Hamper, B. C. Tetrahedron Lett. 1996, 37, 5277-5280. (b) Tietze, L. F.; Steinmetz, A. Synlett 1996, 667-668.
36. For other recent reports of thermolytic cleavage off a polymer support, see refs 14, 18, 19, and: (a) Kolodziej, A. A.; Hamper, B. C. Tetrahedron Lett. 1996, 37, 5277-5280. (b) Tietze, L. F.; Steinmetz, A. Synlett 1996, 667-668.
37. Letsinger, R. L.; Kornet, M. J.; Mahadevan, V.; Jerina, D. M. J. Am. Chem. Soc. 1964, 86, 5163-5165.
38. A TentaGel-derived chloroformate has been utilized as a carbamate linking group for solid-phase synthesis; see: Hauske, J. R.; Dorff, P. Tetrahedron Lett. 1995, 36, 1589-1592.
39. Levine, A. W.; Frech, J. J. Org. Chem. 1972, 37, 1500-1503.
40. Levine, A. W.; Frech, J. J. Org. Chem. 1972, 37, 2455-2460.
41. Triphosgene is available from Aldrich (cat. no. 33, 075-2). Phosgene solutions in either toluene or dichloromethane are also suitable for this transformation.
42. -3 (mmol/g resin)
43. Storage of the phosgenated resin 2 and the carbamate resins 3 at room temperature exposed to air for greater than 1 month has little to no effect on their reactivities.
44. (33) Oxime-derived carbamates of secondary amines do not undergo urea formation upon thermolysis under the standard conditions. This observation is consistent with the accepted mechanism for thermolytic decomposition of the oxime-derived carbamates to give isocyanates (see refs 28 and 29). Mechanistic studies of the cleavage of polymer-supported oxime-derived carbamates indicate isocyanate formation upon thermolysis: Scialdone, M. A.; Hamuro, Y.; DeGrado, W. F. J. Am. Chem. Soc., manuscript in preparation.
45. Argonaut Technologies Inc., San Carlos CA.
46. Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell, J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357-3360.
47. Access to 2-isocyanatopyridine via Curtius rearrangement of 2-picolinoyl azide, see: Otsuji, Y.; Koda, Y.; Kubo, M.; Fukukawa, M.; Imoto, E. Nippon Kagaku Zasshi 1959, 80, 1307-1309.
48. For a review of six-membered heterocyclic isocyanates, see: L'abbe, G. Synthesis 1987, 6, 525-531.
49. The picric acid test was carried out after oxime resin was coupled under standard conditions with Boc-Gly-OH followed by TFA deprotection of the Boc group. See: (a) Scarr, R. B.; Findeis, M. A. Peptide Res. 1990, 3, 238-241. (b) Stewart, J. M.; Young, J. D. Solid-Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984.
50. The picric acid test was carried out after oxime resin was coupled under standard conditions with Boc-Gly-OH followed by TFA deprotection of the Boc group. See: (a) Scarr, R. B.; Findeis, M. A. Peptide Res. 1990, 3, 238-241. (b) Stewart, J. M.; Young, J. D. Solid-Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984.