tert-butyl N-[(1S)-2-phenyl-1-(prop-2-yn-1-ylcarbamoyl)ethyl]carbamate → (S)-tert-Butyl (1-(5-methyloxazol-2-yl)-2-phenylethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl (1-oxo-3-phenyl-1-(prop-2-yn-1-ylamino)propan-2-yl)carbamate (95 mg, 0.31 mmol) in MeCN (1.6 mL) was added gold (III) chloride (9.5 mg, 0.031 mmol). The resulting reaction mixture was stirred at 50° C. overnight and then purified directly using flash chromatography (gradient from 0% to 100% EtOAc/hexanes) to give the title compound (69 mg, 73%) as a colorless oil. %). 1H NMR (CDCl3) δ 7.37-7.17 (m, 3H), 7.05 (d, J=6.4 Hz, 2H), 6.63 (s, 1H), 5.12 (br s, 2H), 3.33-3.01 (m, 2H), 2.27 (d, J=1.1 Hz, 3H), 1.49-1.34 (m, 9H); MS (ESI+) m/z 303.3 (M+H)+.

Provenance & Evidence