Ammonium salts from polymer-bound N-hydroxysuccinimide as solid-supported reagents for EDC-mediated amidations

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 463-466

  Chinchilla, Rafael ^a   Dodsworth, David J ^a   Nájera, Carmen ^a   Soriano, José M ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Amidation; Ammonium salts; N hydroxysuccinimide; Polymers

Indexed keywords

1 ETHYL 3 (3' DIMETHYLAMINOPROPYL)CARBODIIMIDE; AMINO ACID DERIVATIVE; AMMONIUM DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; IMIDE; POLYMER; REAGENT; SODIUM CHLORIDE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; PROTECTION; SYNTHESIS;

EID: 0037433945     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02592-3     Document Type: Article

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26. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
27. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
28. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
29. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
30. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
31. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
32. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
33. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
34. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
35. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
36. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42; (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (d) Brown, R. Contemp. Org. Synth. 1997, 216-237; (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509; (f) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239; (g) Lorsbach, B. A.; Kurth, M. J.; Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320; (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-827; (i) Wenworth, R., Jr.; Janda, K. D. Chem. Commun. 1999, 1917-1924; (j) Brown, A. R. Chem. Rev. 1999, 99, 1549-1581; (k) James, I. W. Tetrahedron 1999, 55, 4855-4946; (l) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074; (m) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
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