Triethylamine → N-(3-acetylthio-2-methylpropanoyl)-N-(3-methylthiopropyl)glycine t-butyl ester

Participants

Reaction Steps

To a solution of N-(3-methylthiopropyl)glycine t-butyl ester (36.4 g, 0.166 mol) and triethylamine (20.2 g, 0.199 mol) in 300 ml of dioxane was added dropwise 3-acetylthio -2-methylpropanoyl chloride (30.0 g, 0.166 mol). After stirring at room temperature for 16 hours the mixture was filtered and concentrated to yield 52.9 g. Purification by medium pressure liquid chromatography eluting with 20% ethyl acetate in hexane gave 18.0 g (30%) of N-(3-acetylthio-2-methylpropanoyl)-N-(3-methylthiopropyl)glycine t-butyl ester as a colorless oil. Rf =0.19 (20% ethyl acetate in hexane).

Provenance & Evidence