Triethylamine → (S)-tert-Butyl 1-(2-(benzo[d]oxazol-2-ylamino)ethylamino)-1-oxopent-4-yn-2-ylcarbamate

Participants

Reaction Steps

A cold mixture of Boc-L-propargyl-glycine (128.2 mg, 0.602 mmol), N-hydroxybenzotriazole hydrate (84.5 mg, 0.625 mmol) and the hydrochloride salt of N1-(benzo[d]oxazol-2-yl)ethane-1,2-diamine (152.3 mg, 0.609 mmol) in dichloromethane (6 mL) was cooled in an ice bath, then treated with triethylamine (0.34 mL, 2.44 mmol) and 1-[3-dimethylaminopropyl]-3-ethyl carbodiimide hydrochloride (119.6 mg, 0.624 mmol). The resulting mixture was stirred for 40 h at room temperature, then diluted with dichloromethane, washed with water, dried over sodium sulfate, filtered and concentrated to yield a residue The residue was purified by flash column chromatography, eluting with 8% methanol in chloroform to yield (S)-tert-butyl 1-(2-(benzo[d]oxazol-2-ylamino)ethylamino)-1-oxopent-4-yn-2-ylcarbamate as a solid.

Provenance & Evidence