Chloromethoxymethyl polystyrene (CMM resin), an acid labile resin for anchoring/cleavage of N-heterocycles and oxygen aromatic compounds

Letters in Organic Chemistry

Volumn 2, Issue 4, 2005, Pages 371-373

  Marfil, Marta ^a   Alberico, Fernando ^a   Álvarez, Mercedes ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Methoxymethyl resin; N heterocycles; Solid phase

Indexed keywords

EID: 33750085213     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178054038975     Document Type: Review

References (41)

1. a) Thompson, L. A.; Ellman, J. A. Chem. Rev., 1996, 96, 555;
2. b) Zaragoza-Dörwald, F. Organic Synthesis on Solid Phase, Wiley-VCh, Weinheim, New York, 2000;
3. c) Seneci, P. Solid Phase Synthesis and Combinatorial Technologies, Wiley-VCh, Weinheim, New York, 2000;
4. d) Forns, P.; Fields, G. B., Solid-Phase Synthesis: A Practical Guide, Ed. Kates, S.A. and Albericio, F. Marcel Dekker, New York, 2000;
5. e) A. Czarnik, Solid Phse Organic Synthesis, Ed. Wiley, New York, 2001;
6. f) Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rev., 2002, 102, 2607-2624.
7. a) Perry, N. B.; Ettouati, L.; Litaudon, M.; Blunt, J. W.; Munro, M. H. G.; Parkin, S.; Hope, H. Tetrahedron, 1994, 50, 3987-3992;
8. b) Trimurtulu, G.; Faulkner, D. J.; Perry, N. B.; Ettouati, L.; Litaudon, M.; Blunt, J. W.; Munro, M. H. G.; Jameson, G. B. Tetrahedron, 1994, 50, 3993-4000;
9. c) Anderson, R. J.; Morris, J. C. Tetrahedron Lett., 2001, 42, 8642;
10. d) Ahaidar, A.; Fernández, D.; Danelón, G.; Cuevas, C.; Manzanares, I.; Albericio, F.; Joule, J. A.; Álvarez, M. J. Org. Chem. 2003, 68, 10020;
11. e) Molina, P.; Fresneda, P. M.; Delgado, S. J. Org. Chem., 2003, 68, 489.
12. a) Faulkner, D. J. Nat. Prod. Rep. 1986, 3, 1;
13. Faulkner, idem, Nat. Prod. Rep., 1987, 4, 539;
14. Faulkner, idem, Nat. Prod. Rep., 1988, 5, 613;
15. Faulkner, idem, Nat. Prod. Rep. 1990, 7, 269;
16. Faulkner, idem, Nat. Prod Rep., 1991, 8, 97;
17. Faulkner, idem, Nat. Prod. Rep., 1992, 9, 323;
18. Faulkner, idem Nat Prod. Rep., 1993, 10, 497;
19. Faulkner, idem, Nat. Prod Rep., 1994, 11, 355;
20. Faulkner, idem, Nat. Prod. Rep., 1995, 12, 223;
21. Faulkner, idem. Nat. Prod. Rep., 1996, 13, 75;
22. Faulkner, idem, Nat. Prod. Rep., 2000, 17, 7;
23. Faulkner, idem, Nat. Prod. Rep., 2001, 18, 1;
24. Faulkner, b) Ishibashi, F.; Miyazaki, Y.; Iwao, M. Chem. Int. Ed., 1997, 36, 155;
25. c) Banwell, M., Flynn, B.; Hockless, D. Chemm. Commun., 1997, 2259;
26. d) Cironi, P.; Manzanares, I.; Albericio, F.; Álvarez, M., Org. Lett., 2003, 5, 2959;
27. e) Marfil, M.; Albericio, F.; Álvarez, M. Tetrahedron, 2004, 60, 8659.
28. a) Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A; Jin, Q. J. Am. Chem. Soc., 1999, 121, 54;
29. b) Baz, J. P.; Millan, F. R.; De Quesada, T.G.; Gravalos, D. C. PCT Int. Appl., (1995), WO 9527730.
30. a) Sundberg, R.; Russell, H. F. J. Org. Chem., 1973, 38, 3324;
31. b) Hall, G. J. H.; Oberholzer, M. E.; Ferreira, D.; Roux, D. G. Tetrahedron Lett., 1976, 1033;
32. c) Süsse, M.; Johne, M.; Hesse, M. Helv. Chim. Acta, 1992, 75, 457.
33. a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 1999, Wiley Intercience Publications, John Wiley & Sons, New York;
34. b) Kocienski, P. "Protecting groups", Second Edition 2000, Ed Thieme Foundations of Organic Chemistry Series, New York.
35. A preliminary report of the present work was presented as a poster at the Eleventh FECHEM Conference on Heterocycles in Bio-organic Chemistry, June 2002, Sitges-Barcelona, Spain.
36. As our experimental studies were completed, we became aware of a related resin (polystyrene bound ethoxymethyl chloride) (Ruhland, T.; Pedersen, H.; Andersen, K. Synthesis, 2003, 2236), which allows the preparation of substituted 1-methylindoles through reductive cleavage. According to authors, all attempts to cleave 1H-indoles from the resin under acid conditions failed due to the formation of undefined side products. In that paper, we were also aware of a patent (Gaitanopoulos, D.E.; Weinstock, J. USA patent WO 95/34813, 1995), where the synthesis of chloromethoxymethyl polystyrene by reaction of hydroxymethyl polystyrene with formaldehyde and hydrochloric acid is reported for the anchoring of carboxylic acids
37. The procedure was analogous as the described in solution by Corey, E. J.; Block, M. G. Tetrahedron Lett., 1975, 16, 3269; Benneche, T.; Strande, P.; Undheim, K. Synthesis, 1983, 762.
38. An aliquot of resin 2 was treated with Boc-Ala-OH/DIPCDI/DMAP (5/5/0.5 equiv. each one) in DCM for 15 min, the sample was hydrolyzed with 12 N HCI- propionic acid (1:1) and the Ala content determined by amino acid analysis.
39. The yield was calculated directly with a small aliquot by amino acid analysis after incorporation of Fmoc-Leu-OH as a cesium salt.
40. The cleavage was done by treatment of the resin with 2M HCl in MeOH at room temperature for 72 h.
41. 2O (0.045 % TFA) and MeCN (0.036 % TFA) as eluents in a gradient (0 - 100 % MeCN) in 15 min.