Triethylamine → HCID 86714597, compound

Participants

Reaction Steps

A solution of 2-(benzyloxycarbonylamino)-4,4,4-trifluoro-2-methylbutanoic acid (1.6 g, 5.2 mmol) in THF (17 ml) was cooled to 0° C. and triethylamine (910 ul, 6.5 mmol) was added, then ethyl chloroformate (624 ul, 6.5 mmol) dropwise over 40 min. A solution of sodium borohydride (491 mg, 13 mmol) in H2O (2.6 ml) was added dropwise over 2 h. The reaction was quenched by the addition of 1 M HCl, stirred for 5 min, and then extracted with EtOAc. The organic layer was washed with sat. NaHCO3, sat. NaCl, dried on Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (15% to 100% EtOAc in hexanes) to afford the title compound as a clear oil (838 mg). 1H NMR (CDCl3, 400 MHz) δ 1.36 (s, 3H), 2.33-2.45 (m, 1H), 2.93-3.03 (m, 1H), 3.62 (br s, 1H), 3.65-3.76 (m, 2H), 5.07-5.10 (m, 3H), 7.28-7.39 (m, 5H). LRMS (ESI/APCI): 292 [M+H]+.

Provenance & Evidence