J. Looker, J. W. Carpenter
Aug 1, 1967
Citations
0
Influential Citations
9
Citations
Journal
Canadian Journal of Chemistry
Abstract
A new preparative procedure for N-(diazoacetyl)glycine ethyl ester is described. The interaction of N-(diazoacetyl)glycine ethyl ester with four phenoxyacetyl chlorides gives the 4-phenoxylderivatives of N-(2-diazo-3-oxobutanoyl)glycine ethyl ester, and with β-(o-methoxyphenoxy)-propionyl chloride yields N-[2-diazo-3-oxo-5-(o-methoxyphenoxy)pentanoyl]glycine ethyl ester. A general chromatographic procedure for separating N-(2-diazo-3-oxoalkanoyl)glycine ethyl esters from N-(chloroacetyl)glycine ethyl ester has been developed. Crotonyl chloride reacts with a 1 mole excess of N-(diazoacetyl)glycine ethyl ester to form N-(2-diazo-3-oxo-4-hexenoyl)glycine ethyl ester, and with a 2 mole excess to form N-{2-diazo-3-oxo-3-[4′-methyl-5′(carboethoxymethyl)carbamoyl-Δ2pyrazolin-3′-yl]propanoyl}glycine ethyl ester, presumably by isomerization of an initially formed Δ1-pyrazoline derivative. The interaction of benzoyl and m-bromobenzoyl bromide with N-(diazoacetyl)glycine ethyl ester results initially in yellow oily ...