1-[2-acetoxymethyl-3-(acetylthio)propanoyl]-L-proline → 1-(2-hydroxymethyl-3-mercaptopropanoyl)-L-proline

Participants

Reaction Steps

N-[2-acetoxymethyl-3-(acetylthio)propanoyl]-L-proline (1.5 g) is dissolved in a mixture of water (12 ml) and concentrated ammonia (12 ml) under a blanket of argon. After one hour, the reaction mixture is concentrated to ca. dryness, diluted with water and the solution applied to a column of cation exchange resin (Dowex 50) in the hydrogen cycle. The water eluate is concentrated to small volume and freeze-dried to yield N-(2-hydroxymethyl-3-mercaptopropanoyl)-L-proline.

Provenance & Evidence