Title

Chemoselective N-Acylation Via Condensations Of N-(Benzoyloxy)Amines And Α-Ketophosphonic Acids Under Aqueous Conditions

Abstract

(Chemical Equation Presented) A new amide-forming reaction with N-benzoyloxyamines and α-ketophosphonic acids was investigated. A mixed solvent of t-BuOH/water (1:1) at 40°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 α-ketophosphonic acids under the conditions tested. Moreover, the α-ketophosphonic acids are more selective than the related α-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. © 2008 American Chemical Society.

Publication Date

8-15-2008

Publication Title

Journal of Organic Chemistry

Volume

73

Issue

16

Number of Pages

6182-6186

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/jo800223j

Socpus ID

50149088823 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/50149088823

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