Water → HCID 12621985, compound

Participants

Reaction Steps

Ethyl oxalyl chloride (212 g) was added dropwise with stirring to a solution of isovalerylalanine (136 g) and pyridine (186.5 g) in anhydrous tetrahydrofuran (500 ml) at a rate sufficient to initiate refluxing. The reaction mixture was stirred and heated at reflux for 5 hours. The cooled reaction mixture was treated with water (1000 ml) and extracted with ethyl acetate (4×400 ml). The combined organic extracts were washed with water (3×200 ml) and dried (anhydrous sodium sulphate). Removal of solvent provided a yellow syrup which was evaporated with benzene (2×200 ml) to yield the isomeric enol esters of the title compound.

Provenance & Evidence