Title

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

Authors

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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