Synthesis of Nα-Tetrachlorophthaloyl (TCP)-Protected Amino Acids under Microwave Irradiation (MWI)

Esther Cros; Marta Planas; Eduard Bardají

doi:10.1055/s-2001-15215

PAPER

Synthesis of N ^α-Tetrachlorophthaloyl (TCP)-Protected Amino Acids under Microwave Irradiation (MWI)

Esther Cros, Marta Planas, Eduard Bardají*
Department of Chemistry, University of Girona, 17071 Girona, Spain
Fax: +34(972)418150; e-Mail: dqebr@xamba.udg.es;

Abstract

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Abstract

A range of N ^α-tetrachlorophthaloyl protected amino acids have been synthesized by an easy and efficient condensation procedure of the corresponding amino acid and tetrachlorophthaloyl anhydride under irradiation in an unmodified commercial microwave oven.

Key words

amino acids - microwave irradiation - protecting groups - phthalimide - tetrachlorophthaloyl

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References

References and Notes

<A NAME="RE00201SS-1">1</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd Ed.: Wiley; New York: 1999.

<A NAME="RE00201SS-2A">2a</A> Debenham JS. Madsen R. Roberts C. Fraser-Reid B. J. Am. Chem. Soc. 1995, 117: 3302

<A NAME="RE00201SS-2B">2b</A> Debenham JS. Fraser-Reid B. J. Org. Chem. 1996, 61: 432

<A NAME="RE00201SS-2C">2c</A> Debenham JS. Debenham SD. Fraser-Reid B. Bioorg. Med. Chem. 1996, 4: 1909

<A NAME="RE00201SS-2D">2d</A> Debenham JS. Rodebaugh R. Fraser-Reid B. Liebigs Ann./Recueil 1997, 791

<A NAME="RE00201SS-3">3</A> Castro-Palomino JC. Schmidt RR. Tetrahedron Lett. 1995, 36: 5343

<A NAME="RE00201SS-4">4</A> Stangier P. Hindsgaul O. Synlett 1996, 179

<A NAME="RE00201SS-5">5</A> El-Naggar AM. Zaher MR. El-Basiouny M. Khalaf NS. Il Farmaco-Ed. Sc. 1984, 39: 154 ; They reported the synthesis in solution of some N-tetrachlorophthaloyl protected amino acids and dipeptide derivatives to test their biological activity against a number of microorganisms. The reported synthesis did not include any deprotection step of the TCP protecting group

<A NAME="RE00201SS-6A">6a</A> Bose AK. Greer F. Price CC. J. Org. Chem. 1958, 23: 1335

<A NAME="RE00201SS-6B">6b</A> Bose AK. Org. Synth., Coll. Vol. V 1973, 973

<A NAME="RE00201SS-7">7</A> Scheehan JC. Chapman DW. Roth RW. J. Am. Chem. Soc. 1952, 74: 3822

<A NAME="RE00201SS-8">8</A> Aguilar N. Moyano A. Pericàs MA. Riera A. Synthesis 1998, 313

<A NAME="RE00201SS-9A">9a</A> Bram G. Loupy A. Majdoub M. Gutiérrez E. Ruiz-Hitzky E. Tetrahedron 1990, 46: 5167

<A NAME="RE00201SS-9B">9b</A> Bose AK. Manhas MS. Banik BK. Robb EW. Res. Chem. Intermed. 1994, 20: 1

<A NAME="RE00201SS-9C">9c</A> Caddick S. Tetrahedron 1995, 51: 10403

<A NAME="RE00201SS-10">10</A> Bose AK. Jayaraman M. Okawa A. Bari SS. Robb EW. Manhas MS. Tetrahedron Lett. 1996, 37: 6989

PAL, peptide amide linker: 5-(4-aminomethyl-3,5-dimethoxyphenoxy)valeric acid; PEG-PS, polyethylene glycol-polystyrene (graft support).

Continuous heating resulted in burning of the reaction mixture.

<A NAME="RE00201SS-13">13</A> Kaiser E. Colescott RL. Bossinger CD. Cook P. Anal. Biochem. 1970, 34: 595

Synthesis of N α -Tetrachlorophthaloyl (TCP)-Protected Amino Acids under Microwave Irradiation (MWI)

Synthesis of N ^α-Tetrachlorophthaloyl (TCP)-Protected Amino Acids under Microwave Irradiation (MWI)