反应详情

To a solution of tert-butyl (2S,3S)-3-(benzyloxy)-4,4,4-trifluoro-1-hydroxybutan-2-ylcarbamate (1.47 g, 4.2 mmol) in acetone (80 mL) was added Jone's reagent (8.2 mL) at 0° C. The mixture was stirred at the same temperature for 3 h until the starting material was completely consumed, then the reaction was quenched by adding isopropanol (5 mL). The reaction mixture was extracted with EtOAc. The extracts were washed with water, brine and dried over Na2SO4. Removal of the solvent gave the crude (2R,3S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)-4,4,4-trifluorobutanoic acid (1.56 g), which was used directly for the following reaction. 1H NMR (400 MHz, CD3OD, δ in ppm) 7.25˜7.34 (m, 5H), 4.76 (d, J=10.9 Hz, 1H), 4.70 (d, J=10.9 Hz, 1H), 4.53 (d, J=6.4 Hz, 1H), 4.32 (m, 1H), 1.41 (s, 9H).

1. customwas completely consumed
2. customthe reaction was quenched
3. additionby adding isopropanol (5 mL)
4. extractionThe reaction mixture was extracted with EtOAc
5. washThe extracts were washed with water, brine
6. dry with materialdried over Na2SO4
7. customRemoval of the solvent