A selective method for the preparation of primary amides: Synthesis of Fmoc-L-4 carboxamidophenylalanine and other compounds

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2501-2504

  Wang, Wei ^a   McMurray, John S ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMMONIUM CHLORIDE; CARBOXYLIC ACID; ESTER; PHENYLALANINE DERIVATIVE;

ACYLATION; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; LYSIS; SYNTHESIS; TEMPERATURE;

EID: 0033605807     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00245-2     Document Type: Article

References (11)

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3. Bodanszky M., "The Practice of Peptide Synthesis", Springer-Verlag: Berlin, 1984, pp 150-151, 173.
4. Galaverva G., Corradini R., Cossena A. and Marchelli R. Int. J. Peptide Protein Res. 1993, 42, 53-57.
5. Chen S. T., Wu S. H. and Wang K. T. Synthesis 1989, 37-38.
6. Analytical HPLC was performed on a Hewlett Packard 1090 liquid Chromatograph using a Vydac C4 column (4.6 x 250 mm). The gradient was 15-75% B/25min with a flow rate of 1.5ml/min (A: 0.1% TFA in water; B: 0.1%TFA in acetonitrile). Elution was monitored with a diode array detector at both 230 nm and 274 nm.
7. (table presented)
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9. 3 (3eq.) in water dioxane (1:1) at room temperature for 4 h to afford 0.21 gm (0.5 mmol) of Fmoc-4-carboxyamidophenylalanine-OH.
10. Matsoukas, J.M.; Agelis, G.; Wahhab, A.; Hondrelis, J.; Panagiotopoulos D.; Yamdagni R.; Wu, Q.; Mavromoustakos, T.; Maia, H.L.S.; Ganter, R.; Moore, G.J. J. Med. Chem. 1995, 38, 4660-4669.
11. Lai, J.H., Marsilje, T.H., Choi, S., Nair, S.A., and Hangauer, D.G. J. Peptide Res. 1998, 51, 271-281.