Chemoselective N-acylation via condensations of N-(benzoyloxy)amines and alpha-ketophosphonic acids under aqueous conditions

    Authors

    J. S. Arora; N. Kaur;O. Phanstiel

    Comments

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    Abbreviated Journal Title

    J. Org. Chem.

    Keywords

    AMINES; ALDEHYDES; HYDROXYPHOSPHONATES; ACYLPHOSPHONATES; HYDROCHLORIDE; DERIVATIVES; OXIDATION; REAGENTS; SALTS; BOND; Chemistry, Organic

    Abstract

    A new amide-forming reaction with N-benzoyloxyamines and alpha-ketophosphonic acids was investigated. A mixed solvent of t-BuOH/water (1:1) at 40 degrees C provided the desired amide in high yield (71-96%). Both phosphonic acids (9, 12, or 13) and their disodium salts (e.g., 10) were shown to react with the respective N-benzoyloxyamines (1b and 4) in excellent yields. The phosphonic acid methyl ester monosodium salt 11 did not react under these conditions. However, compound 11 did provide the desired amide in 22% yield upon addition of 2 equiv of TFA. The N-acylation reaction is highly chemoselective for N-benzoyloxyamines as both aliphatic amines and N-hydroxylamines were shown not to react productively with the alpha-ketophosphonic acids under the conditions tested. Moreover, the alpha-ketophosphonic acids are more selective than the related alpha-ketocarboxylic acid systems, which react with both the N-hydroxylamines and N-benzoyloxyamines. In this regard, this novel phosphonic acid methodology provides a new high-yielding, chemoselective acylating reagent for further study.

    Journal Title

    Journal of Organic Chemistry

    Volume

    73

    Issue/Number

    16

    Publication Date

    1-1-2008

    Document Type

    Article

    Language

    English

    First Page

    6182

    Last Page

    6186

    WOS Identifier

    WOS:000258332500018

    ISSN

    0022-3263

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