Diethylaminoethyl chloride → Benzyl 6-azido-3-(2-diethylaminoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

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Reaction Steps

An ice-cold solution of benzyl 6-azido-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (1 mmol) in anhydrous dimethylformamide (1 ml) is added dropwise to an ice-cold mixture of potassium hydride (1 mmol) in anhydrous dimethylformamide (4 ml). After stirring for several minutes in the cold and under nitrogen, the mixture is treated with diethylaminoethyl chloride and stirred in the cold for 2 hr. The mixture is diluted with ethyl acetate, washed thoroughly with water and brine, dried over magnesium sulfate, and filtered. Evaporation of the solvent in vacuo gives benzyl 6-azido-3-(2-diethylaminoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Provenance & Evidence