Synthesis of N-(3-arylpropyl)amino acid derivatives by sonogashira types of reaction in aqueous media

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2823-2826

  López Deber, M Pilar ^a   Castedo, Luis ^a   Granja, Juan R ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

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ARTICLE;

EID: 0012445118     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0162421     Document Type: Article

References (40)

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9. Alkylation of the amide nitrogen reduces the energy difference between the cis and trans forms to approximately 2.1 kJ/mol compared to ca. 10.9 kJ/mol for conventional amino acids: Stewart, D. E.; Sarkar, A.; Wampler, J. E. J. Mol. Biol. 1990, 214, 253-260.
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13. For an example, see: Schmidt, R.; Kalman, A.; Chung, N. N.; Lemieux, C.; Horvath, C.; Schiller, P. W. Int. J. Pept. Protein Res. 1995, 46, 47-55. N-Methylation of amino acids has also been used to increase the potency or selectivity of a peptide ligand: Ali, F. E.; Bennett, D. B.; Calvo, R. R.; Elliot, J. D.; Hwang, S.-M.; Ku, T. W.; Lago, M. A.; Nichols, A. J.; Romoff, T. T.; Shah, D. H.; Vasko, J. A.; Wong, A. S.; Yellin, T. O.; Yuan, C.-K.; Samanen, J. M. J. Med. Chem. 1994, 37, 769-780. Oligomeric N-substituted glycines (peptoids) have emerged as promising tools for drug discovery; for an example, see: Wu, C. W.; Sanborn, T. J.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2001, 123, 2958-2963.
14. For an example, see: Schmidt, R.; Kalman, A.; Chung, N. N.; Lemieux, C.; Horvath, C.; Schiller, P. W. Int. J. Pept. Protein Res. 1995, 46, 47-55. N-Methylation of amino acids has also been used to increase the potency or selectivity of a peptide ligand: Ali, F. E.; Bennett, D. B.; Calvo, R. R.; Elliot, J. D.; Hwang, S.-M.; Ku, T. W.; Lago, M. A.; Nichols, A. J.; Romoff, T. T.; Shah, D. H.; Vasko, J. A.; Wong, A. S.; Yellin, T. O.; Yuan, C.-K.; Samanen, J. M. J. Med. Chem. 1994, 37, 769-780. Oligomeric N-substituted glycines (peptoids) have emerged as promising tools for drug discovery; for an example, see: Wu, C. W.; Sanborn, T. J.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2001, 123, 2958-2963.
15. For an example, see: Schmidt, R.; Kalman, A.; Chung, N. N.; Lemieux, C.; Horvath, C.; Schiller, P. W. Int. J. Pept. Protein Res. 1995, 46, 47-55. N-Methylation of amino acids has also been used to increase the potency or selectivity of a peptide ligand: Ali, F. E.; Bennett, D. B.; Calvo, R. R.; Elliot, J. D.; Hwang, S.-M.; Ku, T. W.; Lago, M. A.; Nichols, A. J.; Romoff, T. T.; Shah, D. H.; Vasko, J. A.; Wong, A. S.; Yellin, T. O.; Yuan, C.-K.; Samanen, J. M. J. Med. Chem. 1994, 37, 769-780. Oligomeric N-substituted glycines (peptoids) have emerged as promising tools for drug discovery; for an example, see: Wu, C. W.; Sanborn, T. J.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2001, 123, 2958-2963.
16. b are two of the most commonly methods used for the preparation of N-alkylated amino acids: (a) Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. J. Org. Chem. 1996, 61, 6720-6722.
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18. b on solid phase has recently been reported, although the scope of these methods has not been demonstrated yet: (a) Miller, S. C.; Scanlan, T. S. J. Am. Chem. Soc. 1997, 119, 2301-2302.
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31. No significant improvements in yield were obtained using iodoaryl derivatives, despite the latter being more reactive than bromides: Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-CVH: New York, 1998; Chapter 5.
32. For cost reasons, triphenylphosphine and potassium carbonate were used in most of the experiments.
33. We attribute this negative result in base to the low solubility of 6-bromo-2,2′-bipyridine in the solvent mixture.
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40. The cross-coupling reaction of the unprotected tetrapeptide gave lower yield.