Regioselective nitration of N(alpha),N(1)-bis(trifluoroacetyl)-L-tryptophan methyl ester: efficient synthesis of 2-nitro and 6-nitro-N-trifluoroacetyl-L-tryptophan methyl ester

Andrew S Osborne; Phanneth Som; Jessica L Metcalf; Robert S Phillips

doi:10.1016/j.bmcl.2008.09.086

Regioselective nitration of N(alpha),N(1)-bis(trifluoroacetyl)-L-tryptophan methyl ester: efficient synthesis of 2-nitro and 6-nitro-N-trifluoroacetyl-L-tryptophan methyl ester

Bioorg Med Chem Lett. 2008 Nov 1;18(21):5750-2. doi: 10.1016/j.bmcl.2008.09.086. Epub 2008 Sep 26.

Authors

Andrew S Osborne¹, Phanneth Som, Jessica L Metcalf, Robert S Phillips

Affiliation

¹ Department of Chemistry, University of Georgia, Athens, GA 30602, USA.

Abstract

Nitration of N(alpha),N(1)-bis(trifluoroacetyl)-l-tryptophan methyl ester with HNO(3) in acetic anhydride at 0 degrees C provides N(alpha)-trifluoroacetyl-2-nitro-l-tryptophan methyl ester in 67% yield, whereas nitration in trifluoroacetic acid at 0 degrees C gives N(alpha)-trifluoroacetyl-6-nitro-l-tryptophan methyl ester in 69% yield.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Chromatography, High Pressure Liquid
Magnetic Resonance Spectroscopy
Nitrates / chemistry*
Tryptophan / analogs & derivatives*
Tryptophan / chemical synthesis
Tryptophan / chemistry

Substances

Nitrates
tryptophan methyl ester
Tryptophan

Abstract

Publication types

MeSH terms

Substances

Grants and funding