1,2-Dichloroethane → HCID 10041812, compound

Participants

Reaction Steps

A solution of (S)-2-tert-butoxycarbonylamino-4-phenylbutyric acid (500 g, 179 mmol), EDC (37.8 g, 197 mmol), HOBT (41.1 g, 269 mmol) and N,O-dimethylhydroxylamine hydrochloride (19.2 g, 197 mmol) in, dichloromethane (500 mL) was cooled in an ice bath and then treated with a solution of triethylamine (27.5 mL, 197 mmol) in dichloromethane (150 mL). The ice bath was removed and the reaction mixture was stir at room temperature for approximately 12 hours. The mixture was concentrated by rotary evaporation and the residue was treated with ethyl acetate (450 mL), water (300 mL) and saturated sodium bicarbonate until all solids were dissolved. The ethyl acetate layer was separated and washed sequentially with saturated sodium bicarbonate (100 mL), water (100 mL), 1N hydrochloric acid (100 mL), water (100 mL) and brine (50 mL). The solution was dried over anhydrous magnesium sulfate and concentrated to provide tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate (53.41 g, 93% yield) as a clear, colorless oil.

Provenance & Evidence