Triethylamine → HCID 86594562, compound

Participants

Reaction Steps

Triethylamine (0.16 mL, 1.1 mmol) was added dropwise to a solution of N-(4-bromoisothiazol-5-yl)leucine (92 mg, 0.31 mmol), aminoacetonitrile hydrochloride (58 mg, 0.63 mmol) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (180 mg, 0.35 mmol) in N, N-dimethylformamide (1.0 mL) at 0° C. After stirring at rt for 3 h, the reaction vessel contents were poured into water and extracted with a 1:1 mixture of ether and ethyl acetate (3×). The combined extracts were washed with saturated sodium bicarbonate solution, then with saturated sodium chloride solution, and dried (Na2SO4). Concentration under reduced pressure and flash chromatography of the residue on silica gel eluting with a mixture of ethyl acetate and hexanes (2:3) afforded 91 mg of N2-(4-bromoisothiazol-5-yl)-N1-(cyanomethyl)leucinamide as a colorless foam.

Provenance & Evidence