Triethylamine → (S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

Participants

Reaction Steps

2-Piperidino-1,3-benzoxazole (203.6 mgs, 1.00 mmol), N-hydroxybenzotriazole hydrate (138.2 mg, 1.02 mmol) and Boc-β-(2-thienyl)-L-alanine (272.6 mgs, 1.00 mmol) in dichloromethane (10 mL) was cooled in an ice bath, then treated with triethylamine (0.30 mL, 2.15 mmol) and 1-[3-dimethylaminopropyl]-3-ethyl carbodiimide hydrochloride (199.5 mg, 1.04 mmol). The resulting mixture was stirred overnight at room temperature. After 18 h, the resulting mixture was diluted with chloroform and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated to a residue. The residue was purified by flash column chromatography, eluting with 3% methanol in chloroform to yield (S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate as a colorless glass.

Provenance & Evidence