Acetic Acid → HCID 44594157, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0-5° C.) solution of (S)-2-(dibenzylamino)pentanal in dichloromethane (210 mL) was added cyclopropylisonitrile followed by acetic acid at 0-5° C. The reaction mixture temperature was raised to 25-30° C. over 40-60 minutes, and stirred for 16-18 hours at 25-30° C. Progress of the reaction was monitored by TLC analysis. When the reaction was complete, the mixture was cooled to 0-5° C., and saturated sodium bicarbonate solution (200 mL) was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were washed with water (1×200 mL), brine (1×200 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product thus obtained was slurried in hexane (150 mL) and stirred for one hour at 25-35° C. The slurry was filtered and the solid washed with hexane and dried under reduced pressure to provide 17.0 g of (2S,3S)-1-(cyclopropylamino)-3-(dibenzylamino)-1-oxohexan-2-yl acetate as a white solid.

Provenance & Evidence