Synthesis and NMR characteristics of  N ‐acetyl‐4‐nitro,  N ‐acetyl‐5‐nitro,  N ‐acetyl‐6‐nitro and  N ‐acetyl‐7‐nitrotryptophan methyl esters | Zendy

King Russell R. | Zendy; Calhoun Larry A. | Zendy

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Synthesis and NMR characteristics of N ‐acetyl‐4‐nitro, N ‐acetyl‐5‐nitro, N ‐acetyl‐6‐nitro and N ‐acetyl‐7‐nitrotryptophan methyl esters

Author(s) -

King Russell R.,

Calhoun Larry A.

Publication year - 2009

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.2377

Subject(s) - chemistry , nitro , methanol , proton nmr , acetoacetic ester synthesis , medicinal chemistry , stereochemistry , organic chemistry , alkyl

N ‐acetyl‐4‐nitrotryptophan methyl ester (2), N ‐acetyl‐5‐nitrotryptophan methyl ester (3), N ‐acetyl‐6‐nitrotryptophan methyl ester (4) and N ‐acetyl‐7‐nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF 3 ‐methanol. Assignments of the 1 H and 13 C NMR chemical shifts were made using a combination of 1 H– 1 H COSY, 1 H– 13 C HETCOR and 1 H– 13 C selective INEPT experiments. Copyright © 2008 Crown in the right of Canada. Published by John Wiley & Sons, Ltd

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