反应详情

温度

60 °C

A mixture of N-((2R,3S)-3-(3-(cyclohexylmethoxy)phenyl)-3-hydroxy-2-methylpropyl)benzamide (0.179 g, 0.47 mmol), hydrazine monohydrate (0.2 mL), aqueous solution of NaOH (50% w/w, 0.5 mL) and NaOEt (30% in MeOH, 1 mL) was heated at 60° C. under argon for 6 days. The reaction mixture was concentrated under reduced pressure, brine added and the product was extracted into MTBE. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (5% 7N NH/MeOH in CH2Cl2) to give Example 76 as a colorless oil. Yield (0.049 g, 38%). 1H NMR (400 MHz, DMSO-d6) δ 7.15 (t, J=8.0 Hz, 1H), 6.78-6.81 (m, 2H), 6.88-6.72 (m, 1H), 4.60 (d, J=4.1 Hz, 1H), 3.71 (d, J=6.5 Hz, 2H), 2.56 (dd, J=6.3 Hz, 12.5 Hz, 1H), 2.40 (dd, J=6.1 Hz, 12.5 Hz, 1H), 1.50-1.84 (m, 7H), 1.08-1.27 (m, 4H), 0.96-1.07 (m, 2H), 0.66 (d, J=6.9 Hz, 3H); ESI MS 278.5 [M+H]+. Chiral HPLC: 92.6%, tR=10.0 min.

1. concentrationThe reaction mixture was concentrated under reduced pressure, brine
2. additionadded
3. extractionthe product was extracted into MTBE
4. concentrationThe mixture was concentrated under reduced pressure
5. customthe residue was purified by flash chromatography (5% 7N NH/MeOH in CH2Cl2)