2-Ethoxypyridine 1-Oxide

[3445-09-8]  · C7H9NO2  · 2-Ethoxypyridine 1-Oxide  · (MW 139.16)

(acyl activating agent for peptide synthesis;1 catalyst for phosphotriester bond formation2)

Physical Data: mp 72-74 °C.

Solubility: sol ethanol, acetic acid.

Preparative Methods: from 2-ethoxypyridine and Hydrogen Peroxide3 or 2-chloropyridine 1-oxide and ethanolic Sodium Ethoxide.4

Peptide Synthesis.1

Reacts with acid chlorides to give activated esters which can be condensed with amino acids, giving 1-hydroxy-2(1H)-pyridone as a water-soluble byproduct (eq 1). This is an advantage over coupling using 1,3-Dicyclohexylcarbodiimide because of the easier separation of byproducts.

Phosphotriester Bond Formation.2

One of a range of oxygen-nucleophilic catalysts for phosphotriester bond formation which gives few byproducts. 4-Ethoxypyridine 1-oxide is even faster.2

1. Paquette, L. A. JACS 1965, 87, 5186.
2. Efimov, V. A.; Chakhmakhcheva, O. G.; Ovchinnikov, Y. A. Nucleic Acids Res. 1985, 13, 3651.
3. Newbold, G. T.; Spring, F. S. JCS 1948, 1864.
4. Gardner, J. N.; Katritzky, A. R. JCS 1957, 4375.

Kenneth A. Murray

University of Cambridge, UK

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