Triethylamine → N-(cyanomethyl)-4-methyl-2-(3-phenylphenyl)pentanamide

Participants

Reaction Steps

A solution comprised of 2-biphenyl-3-yl-4-methylpentanoic acid (0.251 mg, 0.91 mmol), prepared as in Example 3, in DMF (5 mL) was treated with aminoacetonitrile (180 mg, 2 mmol), PyBOP (520 mg 1 mmol) and triethylamine (500 μL, 3 mmol). The mixture was stirred for 4 hours and then diluted with water (50 mL) and ethyl acetate (20 mL). The organic layer was separated, washed with 1 M saturated sodium bicarbonate solution, 1 M hydrochloric acid solution, water and brine, dried (MgSO4) and concentrated. The residue was recrystallized from 30% ethyl acetate in hexane to provide 2-biphenyl-3-yl-N-cyanomethyl-4-methylpentanamide (300 mg, 0.89 mmol). 1H NMR (DMSO-d6): 1.01 (d, 6H), 1.81-1.85 (m, 3H), 3.73 (dd, 1H), 4.35 (m, 2H), 7.12 (d, 1H), 7.24-7.37 (m, 8H) 8.31 (s, 1H). LCMS: 307.3 (M+H+).

Provenance & Evidence