Triethylamine → N-(cyanomethyl)-4-methyl-2-(2-phenyl-1,3-thiazol-4-yl)pentanamide

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Reaction Steps

A solution comprised of 4-methyl-2-(2-phenylthiazol-4-yl)pentanoic acid (150 mg, 0.6 mmol), prepared as in Example 5, in DMF (5.0 mL) was treated with PyBOP (300 mg, 0.7 mmol), aminoacetonitrile hydrochloride (100 mg, 1 mmol) and triethylamine (250 μL, 1.5 mmol). The mixture was stirred for 3 hours and then partitioned between water (20 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with 1 M saturated sodium bicarbonate solution, 1 M hydrochloric acid solution and water, dried (MgSO4) and concentrated. Product was purified from the residue by flash column on silica gel (60° A) with 40% ethyl acetate in hexane to provide N-cyanomethyl-4-methyl-2-(2-phenylthiazol-4-yl)pentanamide (120 mg, 0.46 mmol). Rf 0.30. 1H NMR (DMSO-d6): 1.01 (m, 6H), 1.31-1.59 (m, 3H), 3.91 (m, 1H), 4.14 (s, 2H), 7.44 (m, 4H), 7.81 (m, 2H), 8.61 (s, 1H). LCMS: 312.2.0 (M+H+).

Provenance & Evidence