Acetic Acid → ethyl N-{4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}glycinate

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Reaction Steps

4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzaldehyde (68 mg, 0.22 mmol) was dissolved in 1,2-dichloroethane (2.2 mL) and treated with ethyl aminoacetate hydrochloride (34 mg, 0.28 mmol) and acetic acid (25 uL, 0.44 mmol). The solution was stirred at ambient temperatures for 30 minutes and treated with sodium triacetoxyborohydride (51 mg, 0.24 mmol). The mixture was stirred at ambient temperature until complete, diluted with ethyl acetate (50 mL) and washed with sodium bicarbonate (2×30 mL, aqueous saturated). The organic extract was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 97:3; dichloromethane:methanol) to afford the titled compound as a clear oil.

Provenance & Evidence