Water → HCID 20285448, compound

Participants

Reaction Steps

To a solution of N-(3-acetylthio-2-methylpropanoyl)-N-cyclohexylglycine t-butyl ester (36.4 g, 0.101 mol) in 300 ml of methylene chloride was added trimethylsilyl iodide (20.4 g, 0.102 mol). After stirring at room temperature for 1.75 hours 50 ml of water was added, followed in 10 min. by 500 ml of saturated sodium bicarbonate solution. An emulsion formed which was separated by centrifuging. The aqueous solution was separated, acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The extracts were dried, filtered, and concentrated to yield 25.6 g (83.4%) of N-(3-acetylthio-2-methylpropanoyl)-N-cyclohexylglycine as a pale yellow oil. The compound was characterized as its DCHA salt, prepared by dissolving the acid in ether and adding DCHA to pH 8-9. The salt was isolated as a white crystalline solid, m.p. 142°-144°.

Provenance & Evidence