Triethylamine → HCID 69195805, compound

Participants

Reaction Steps

A mixture of tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate (1.0 g, 3.3 mmol) and 3-methoxybenzylamine (1.8 g, 13.3 mmol) in isopropyl alcohol (30 ml) was stirred at room temperature for 6.5 h. The reaction mixture was diluted with EtOAc (100 ml) and washed with 1 N HCl (3×30 ml), sat'd aq. NaHCO3 (1×50 ml) and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to yield an off white solid. The residue was dissolved in THF (20 ml) and chilled to 0° C. followed by the addition of Et3N (0.6 ml, 4.4 mmol) and benzylchloroformate (0.5 ml, 3.6 mmol). The reaction mixture was warmed spontaneously for 3 h. The reaction mixture was diluted with EtOAc, washed with 1N HCl, NaHCO3, and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. Flash chromatography 30% EtOAC/Heptanes yields 1.3 g (70%) of [3-tert-butoxycarbonylamino-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxybenzyl)-carbamic acid benzyl ester. MS (ESI+) for C31H36F2N2O6 m/z 570.8 (M+H)+.

Provenance & Evidence