Hydrochloric Acid → N-[(1S)-3-hydroxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide hydrochloride

Participants

Reaction Steps

A solution was made containing a compound of general structure (V) (Intermediate 6, 0.788 g, 2.15 mmol), e.g., tert-butyl 2-({[(1S)-3-hydroxy-1-phenylpropyl]amino}carbonyl)-1,3-thiazolidine-3-carboxylate, in anhydrous DCM (50 ml). At 0° C., 4M HCl solution in dioxane (50 ml) was added, or alternatively, HCl gas, previously dried with a H2SO4 cc trap, was bubbled slowly through the reaction and deprotection was monitored by TLC using cyclohexane/ethyl acetate (1/1) and stained with a pancaldi solution. After approximately 45 minutes, TLC showed no remaining starting materiel and DCM was then evaporated in vacuo without heating to avoid salt decomposition. More DCM (20 ml) was then added and evaporated again in vacuo to remove remaining potential HCl (2-3 times). The desired product, e.g., N-[(1S)-3-hydroxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide hydrochloride, was isolated as a white solid and used for the next step without further purification and characterization.

Provenance & Evidence