Sodium ethoxide → (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-ethoxymethyl-isonicotinamide

Participants

Reaction Steps

To a solution of 50 mg (0.12 mmol) (+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide in 2 ml ethanol was added 1.32 ml (3.57 mmol) sodium ethylate solution (2.71 M solution in ethanol) and the mixture ultrasonicated at room temperature for 2 h. The reaction mixture was then poured onto water and extracted three times with dichloromethane. The organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/1 acetone/heptane) followed by trituration in ether afforded 35 mg (68%) (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-ethoxymethyl-isonicotinamide as an off-white solid. [α]D20=+60.7° (c=0.94, CHCl3), ES-MS m/e (%): 430 (M+H+, 100).

Provenance & Evidence