Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

To a solution of sodium hydroxide (2 g) in methanol (100 ml) were added n-butylbromide (2 g) and (R)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-3-mercapto-2-propanol (II) obtained in Example 2 at a temperature of 20°-25° C. in nitrogen atmosphere. The mixture was stirred at 25°-30° C. for 5 hours and then concentrated under reduced pressure. The residue was treated with water (50 ml) and extracted with dichloromethane (50 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to give an oil. The oil was dissolved in diethyl ether (20 ml), and hydrogen chloride gas was introduced thereto. Precipitated crystals were collected by filtration and dried to give (R)-3-(n-butylthio)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (I: n=3) hydrochloride (3.4 g). Yield, 86.8%. M.P., 168°-169° C. [α]D20 -89.7° (c=1, methanol). The optical purity of the product was not less than 99% determined by high performance liquid chromatography.

Provenance & Evidence