Alternative Pathways in Cesium Carbonate-Promoted Reactions of tert-Butyl 2-[(Diphenylmethylidene)amino]acetate with 2-Methyl-3-{[tert-butyl(dimethyl)silyl]oxy}propanoyl and Acetyl Chlorides

Abstract

The reaction of tert-butyl 2-[(diphenylmethylidene)amino]acetate with 2-methyl-3-{[tert-butyl­(dimethyl)silyl]oxy}propanoyl chloride in methylene chloride in the presence of cesium carbonate afforded the corresponding β-lactam and acetylglycine derivative. Acetyl chloride reacted with tert-butyl 2-[(diphenyl­methyli­dene)amino]acetate to produce tert-butyl 2-(acetamido)acetate as the only product with high chemo­selectivity.