Acetone → n-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]-benzyloxycarboxamide

Participants

Reaction Steps

2,2-Dimethyl-3-(naphthalen-2-yl)propionic acid (205.4 g) obtained in Step 10 was dissolved in water (173 ml), triethylamine (131 ml) and acetone (800 ml), and a solution of ethyl chlorocarbonate (101.5 ml) in acetone (400 ml) was added under ice-cooling. A solution of sodium azide (73.1 g) in water (400 ml) was added dropwise, and the reaction mixture was stirred at room temperature for 2 hr. To the reaction mixture were added water (1.5 L) and toluene (1.2 L), and the organic layer was separated from the aqueous layer. The organic layer was washed twice with water and three times with saturated brine, and dried over anhydrous sodium sulfate. After the drying agent was filtered off, the filtrate was heated to 100° C. over 4 hr under an argon atmosphere, and stirred at 100° C. for 1 hr. The reaction mixture was concentrated under reduced pressure and benzyl alcohol (500 ml) was added. The mixture was stirred at 105° C. for 1 day. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and n-hexane were added to the obtained residue. The solution was treated with activated carbon and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to give the title compound (240.5 g).

Provenance & Evidence