Hydrochloric Acid → HCID 86666178, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere N,N-thiocarbonyldiimidazole (97.0 g, 0.55 mol) and THF (470 mL) are added and the mixture is stirred for 15-30 min. The mixture is cooled to −10 to 0° C., a solution of (S)-4-methoxybutan-2-amine (46.9 g, 0.455 mol) in methyl tert-butyl ether (389 mL) is added, and the reaction mixture is warmed to 10-20° C. The reaction mixture is stirred at this temperature for 15-20 h, and then is cooled to 0-10° C. Hydrochloric acid (275 mL, 4 N in water) is added to arrive at a pH of 1 to 2. The reaction mixture is warmed to RT and the layers are separated. The aqueous layer is extracted with ethyl acetate (235 mL) and the organic layers are combined and washed with water (140 mL). The organic solution is concentrated under reduced pressure below 45° C., ethyl acetate (211.5 mL) is added, and the solution is concentrated under reduced pressure below 45° C. twice, and ethyl acetate (235 mL) is added. Sodium thiosulfate (32.3 g, 227.0 mmol) is added, the solution is filtered, and the filtercake is washed with ethyl acetate (104 mL). The filtrate is concentrated under reduced pressure below 45° C. to furnish the title compound as a yellow oil (55.0 g, 77%).

Provenance & Evidence