A ROMPGEL-supported N-hydroxysuccinimide: A host of acylations with minimal purification

Organic Letters

Volumn 2, Issue 3, 2000, Pages 261-264

  Barrett, Anthony G M ^a   Cramp, Susan M ^b   Roberts, Richard S ^a   Zecri, Frederic J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Rhone Poulenc Agriculture Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000027580     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991208w     Document Type: Article

References (54)

1. Polymer-supported Reactions in Organic Synthesis; Hodge, P., Sherrington, D. C., Eds.; John Wiley & Sons: New' York, 1980. Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 81, 557. Synthesis and Separations Using Functionalised Polymers; Sherrington, D. C., Hodge, P., Eds.: John Wiley & Sons: New York, 1988.
2. Polymer-supported Reactions in Organic Synthesis; Hodge, P., Sherrington, D. C., Eds.; John Wiley & Sons: New' York, 1980. Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 81, 557. Synthesis and Separations Using Functionalised Polymers; Sherrington, D. C., Hodge, P., Eds.: John Wiley & Sons: New York, 1988.
3. Polymer-supported Reactions in Organic Synthesis; Hodge, P., Sherrington, D. C., Eds.; John Wiley & Sons: New' York, 1980. Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 81, 557. Synthesis and Separations Using Functionalised Polymers; Sherrington, D. C., Hodge, P., Eds.: John Wiley & Sons: New York, 1988.
4. Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18. Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320. Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 997. Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251. Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 1253. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
5. Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18. Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320. Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 997. Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251. Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 1253. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
6. Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18. Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320. Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 997. Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251. Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 1253. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
7. Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18. Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320. Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 997. Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251. Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 1253. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
8. Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18. Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320. Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 997. Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251. Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 1253. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
9. Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18. Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320. Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 997. Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251. Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 1253. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
10. Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567.
11. Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. Curran, D. P.; Hadida, S. J. Org. Chem. 1996, 61, 6480. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 2292.
12. Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. Curran, D. P.; Hadida, S. J. Org. Chem. 1996, 61, 6480. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 2292.
13. Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. Curran, D. P.; Hadida, S. J. Org. Chem. 1996, 61, 6480. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 2292.
14. Perrier, H.; Labelle, M. J. Org. Chem. 1999, 64, 2110. Kiankarimi, M.; Lowe, R.; McCarthy, J. R.; Whitten, J. P. Tetrahedron Lett. 1999, 40, 4497. Starkey, G. W.; Parlow, J. J.; Flynn, D. L. Bioog. Med. Chem. Lett. 1998, 8, 2385.
15. Perrier, H.; Labelle, M. J. Org. Chem. 1999, 64, 2110. Kiankarimi, M.; Lowe, R.; McCarthy, J. R.; Whitten, J. P. Tetrahedron Lett. 1999, 40, 4497. Starkey, G. W.; Parlow, J. J.; Flynn, D. L. Bioog. Med. Chem. Lett. 1998, 8, 2385.
16. Perrier, H.; Labelle, M. J. Org. Chem. 1999, 64, 2110. Kiankarimi, M.; Lowe, R.; McCarthy, J. R.; Whitten, J. P. Tetrahedron Lett. 1999, 40, 4497. Starkey, G. W.; Parlow, J. J.; Flynn, D. L. Bioog. Med. Chem. Lett. 1998, 8, 2385.
17. Benzylidenebis(tricyclohexylphosphine)dichlororuthenium 4 is commercially available from Fluka.
18. Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zecri, F. J. Org. Lett. 1999, 1, 579. Barrett, A. G. M.; Cramp. S. M.; Roberts, R. S. Org. Lett. 1999, 1, 1083.
19. Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zecri, F. J. Org. Lett. 1999, 1, 579. Barrett, A. G. M.; Cramp. S. M.; Roberts, R. S. Org. Lett. 1999, 1, 1083.
20. The polymer loading is equal to the molarity of the monomer.
21. Nahn, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
22. For recent uses of functionalized ROM-polymers, see; Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101, and references therein. Buchmeiser, M. R.; Seeber, G.; Mupa, M.; Bonn, G. K. Chem. Mater. 1999, 11, 1533. Strong, L. E.; Kiessling, L. L. J. Am. Chem. Soc. 1999, 121, 6193. Bolm, C.; Dinter, C. L.; Seger, A.; Höcker, H.; Brozio, J. J. Org. Chem. 1999, 64, 5730. Arimoto, H.; Nishimura, K.; Kinumi, T.; Hayakawa, I.; Uemura, D. Chem. Commun. 1999, 1361.
23. For recent uses of functionalized ROM-polymers, see; Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101, and references therein. Buchmeiser, M. R.; Seeber, G.; Mupa, M.; Bonn, G. K. Chem. Mater. 1999, 11, 1533. Strong, L. E.; Kiessling, L. L. J. Am. Chem. Soc. 1999, 121, 6193. Bolm, C.; Dinter, C. L.; Seger, A.; Höcker, H.; Brozio, J. J. Org. Chem. 1999, 64, 5730. Arimoto, H.; Nishimura, K.; Kinumi, T.; Hayakawa, I.; Uemura, D. Chem. Commun. 1999, 1361.
24. For recent uses of functionalized ROM-polymers, see; Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101, and references therein. Buchmeiser, M. R.; Seeber, G.; Mupa, M.; Bonn, G. K. Chem. Mater. 1999, 11, 1533. Strong, L. E.; Kiessling, L. L. J. Am. Chem. Soc. 1999, 121, 6193. Bolm, C.; Dinter, C. L.; Seger, A.; Höcker, H.; Brozio, J. J. Org. Chem. 1999, 64, 5730. Arimoto, H.; Nishimura, K.; Kinumi, T.; Hayakawa, I.; Uemura, D. Chem. Commun. 1999, 1361.
25. For recent uses of functionalized ROM-polymers, see; Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101, and references therein. Buchmeiser, M. R.; Seeber, G.; Mupa, M.; Bonn, G. K. Chem. Mater. 1999, 11, 1533. Strong, L. E.; Kiessling, L. L. J. Am. Chem. Soc. 1999, 121, 6193. Bolm, C.; Dinter, C. L.; Seger, A.; Höcker, H.; Brozio, J. J. Org. Chem. 1999, 64, 5730. Arimoto, H.; Nishimura, K.; Kinumi, T.; Hayakawa, I.; Uemura, D. Chem. Commun. 1999, 1361.
26. For recent uses of functionalized ROM-polymers, see; Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101, and references therein. Buchmeiser, M. R.; Seeber, G.; Mupa, M.; Bonn, G. K. Chem. Mater. 1999, 11, 1533. Strong, L. E.; Kiessling, L. L. J. Am. Chem. Soc. 1999, 121, 6193. Bolm, C.; Dinter, C. L.; Seger, A.; Höcker, H.; Brozio, J. J. Org. Chem. 1999, 64, 5730. Arimoto, H.; Nishimura, K.; Kinumi, T.; Hayakawa, I.; Uemura, D. Chem. Commun. 1999, 1361.
27. Hermanson, G. T. Bioconjugate Techniques; Academic Press: San Diego, 1996.
28. 1-Hydroxy-2,5-dioxo-3-pyrrolidinesulfonic acid, monosodium salt. Staros, J. V. Biochemistry 1982, 21, 3950.
29. Laufer, D. A.; Chapman, T. M.; Marlborough, D. I.; Vaidya, V. M.; Blout, E. R. J. Am. Chem. Soc. 1968, 90, 2696.
30. Akiyama, M.; Narita, M.; Okawara, M. J. Polym. Sci. A1 1969, 7, 1299. Akiyama, M.; Yanagisawa, Y.; Okawara, M. J. Polym. Sci. A1 1969, 7, 1905. Akiyama, M.; Shimizu, K.; Narita, M. Tetrahedron Lett. 1970, 1015.
31. Akiyama, M.; Narita, M.; Okawara, M. J. Polym. Sci. A1 1969, 7, 1299. Akiyama, M.; Yanagisawa, Y.; Okawara, M. J. Polym. Sci. A1 1969, 7, 1905. Akiyama, M.; Shimizu, K.; Narita, M. Tetrahedron Lett. 1970, 1015.
32. Akiyama, M.; Narita, M.; Okawara, M. J. Polym. Sci. A1 1969, 7, 1299. Akiyama, M.; Yanagisawa, Y.; Okawara, M. J. Polym. Sci. A1 1969, 7, 1905. Akiyama, M.; Shimizu, K.; Narita, M. Tetrahedron Lett. 1970, 1015.
33. Adamczyk, M.; Fishpaugh, J. R.; Mattingly, P. G. Tetrahedron Lett. 1999, 40, 463. Adamczyk, M.; Fishpaush, J. R.; Mattingly, P. G. Bioorg. Med. Chem. Lett. 1999, 9, 217.
34. Adamczyk, M.; Fishpaugh, J. R.; Mattingly, P. G. Tetrahedron Lett. 1999, 40, 463. Adamczyk, M.; Fishpaush, J. R.; Mattingly, P. G. Bioorg. Med. Chem. Lett. 1999, 9, 217.
35. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1965, 87, 4646. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1966, 88, 3164. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1968, 90, 2953. Panse, G. T.; Laufer, D. A. Tetrahedron Lett. 1970, 4181. Kalir, R.; Fridkin, M.; Patchornik, A. Eur: J. Biochem. 1974, 42, 151.
36. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1965, 87, 4646. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1966, 88, 3164. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1968, 90, 2953. Panse, G. T.; Laufer, D. A. Tetrahedron Lett. 1970, 4181. Kalir, R.; Fridkin, M.; Patchornik, A. Eur: J. Biochem. 1974, 42, 151.
37. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1965, 87, 4646. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1966, 88, 3164. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1968, 90, 2953. Panse, G. T.; Laufer, D. A. Tetrahedron Lett. 1970, 4181. Kalir, R.; Fridkin, M.; Patchornik, A. Eur: J. Biochem. 1974, 42, 151.
38. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1965, 87, 4646. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1966, 88, 3164. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1968, 90, 2953. Panse, G. T.; Laufer, D. A. Tetrahedron Lett. 1970, 4181. Kalir, R.; Fridkin, M.; Patchornik, A. Eur: J. Biochem. 1974, 42, 151.
39. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1965, 87, 4646. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1966, 88, 3164. Fridkin, M.; Patchornik, A.; Katchalski, E. J. Am. Chem. Soc. 1968, 90, 2953. Panse, G. T.; Laufer, D. A. Tetrahedron Lett. 1970, 4181. Kalir, R.; Fridkin, M.; Patchornik, A. Eur: J. Biochem. 1974, 42, 151.
40. Wieland, T.; Birr, C. Angew. Chem., Int. Ed. Engl. 1966, 5, 310. Marshall, D. L.; Liener, I. E. J. Org. Chem. 1970, 35, 867. Flanigan, E.; Marshall, G. R. Tetrahedron Lett. 1970, 2403.
41. Wieland, T.; Birr, C. Angew. Chem., Int. Ed. Engl. 1966, 5, 310. Marshall, D. L.; Liener, I. E. J. Org. Chem. 1970, 35, 867. Flanigan, E.; Marshall, G. R. Tetrahedron Lett. 1970, 2403.
42. Wieland, T.; Birr, C. Angew. Chem., Int. Ed. Engl. 1966, 5, 310. Marshall, D. L.; Liener, I. E. J. Org. Chem. 1970, 35, 867. Flanigan, E.; Marshall, G. R. Tetrahedron Lett. 1970, 2403.
43. Kalir, R.; Warshawsky, A.; Fridkin, M.; Patchornik, A. Eur. J. Biochem. 1975, 59, 55. Mokotoff, M.; Patchornik, A. Int. J. Pept. Protein Res. 1983, 21, 145.
44. Kalir, R.; Warshawsky, A.; Fridkin, M.; Patchornik, A. Eur. J. Biochem. 1975, 59, 55. Mokotoff, M.; Patchornik, A. Int. J. Pept. Protein Res. 1983, 21, 145.
45. Shai, Y.; Jacobson, K. A.; Patchornik, A. J. Am. Chem. Soc. 1985, 107, 4249.
46. Masala, S.; Taddei, M. Org. Lett. 1999, 1, 1355.
47. Ang, T. L.; Harwood, H. J. J. Macromol. Sci. Chem. A 1973, 7. 1079. Shambhu, M. B.; Digenis, G. A. Tetrahedron Lett. 1973, 1627. Martin, G. E.; Shambhu, M. B.; Shakhshir, S. R.; Digenis, G. A. J. Org. Chem. 1978, 43, 4571.
48. Ang, T. L.; Harwood, H. J. J. Macromol. Sci. Chem. A 1973, 7. 1079. Shambhu, M. B.; Digenis, G. A. Tetrahedron Lett. 1973, 1627. Martin, G. E.; Shambhu, M. B.; Shakhshir, S. R.; Digenis, G. A. J. Org. Chem. 1978, 43, 4571.
49. Ang, T. L.; Harwood, H. J. J. Macromol. Sci. Chem. A 1973, 7. 1079. Shambhu, M. B.; Digenis, G. A. Tetrahedron Lett. 1973, 1627. Martin, G. E.; Shambhu, M. B.; Shakhshir, S. R.; Digenis, G. A. J. Org. Chem. 1978, 43, 4571.
50. The ROMPGELs 3 obtained were sometimes soluble in dichloromethane or ethyl acetate depending the nature of the acyl substituent. In these cases, copolymerisaztion of the monomers 2 with norbornadiene (5 mol %) yielded an insoluble polymer.
51. Xu, W.; Mohan, R.; Morrissey, M. M. Tetrahedron Lett. 1997, 38, 7337.
52. 3·3HF complex was the reagent of choice since all byproducts were liquids. Desilylation with tetrabutylammonium fluoride (TBAF) gave a crystalline polymer, presumably due to ammonium salts trapped in the resin, which led to poorer yields in subsequent acylation reactions.
53. Amides 7cB, 7cC, 7dB, 7dC, 7eC, 7eC, and urea 7hA were synthesized in 79-97% yield and in greater than 95% purity by GCMS.
54. ROMPGEL 3c (1.2 equiv) was treated with amine 6A to give amide 7cA (97% yield), hydrolyzed to ROMPGEL 8, reacylated with acid chloride 5a, and used to make amide 7aA (95% yield, > 95% purity). No cross contamination was observed.