Benzyl chloroformate → CBZ-L-ALANINOL

To a solution of (S)-(+)-2-amino-1-propanol (200 g, 2.66 mol) in purified water (400 mL) was added sodium bicarbonate (246 g, 2.93 mol). To this mixture was added benzyl chloroformate (500 g, 2.93 mol) in tetrahydrofuran (800 mL) at an internal temperature of 20° C. or below. Subsequently, the resulting reaction mixture was stirred at room temperature for 16 hours. After confirming the disappearance of the starting materials by TLC, the reaction mixture was then extracted with ethyl acetate. The organic layer was washed with 0.5 N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, and then dried over anhydrous sodium sulfate. The resulting solution was filtered and concentrated under reduced pressure. The residue was crystallized from petroleum ether to give the target product as a white solid (403 g, yield 72.3%).

1. customSubsequently, the resulting reaction mixture
2. extractionthe reaction mixture was then extracted with ethyl acetate
3. washThe organic layer was washed with 0.5 N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationThe resulting solution was filtered
6. concentrationconcentrated under reduced pressure
7. customThe residue was crystallized from petroleum ether

ORD record

ord-dc19acee24d3492390588de04e1f0683

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045460B2