Sodium hydride → HCID 86718370, compound

Participants

Reaction Steps

To a solution of 2.16a in THF (6 mL) was added NaH (120 mg, 60% in mineral oil, 3 mmol, 8 equiv.) at 0° C. The mixture was stirred at room temperature for 30 minutes. After cooled down to 0° C. in an ice bath, to the solution was added (2S,3S)-3-((tert-butoxycarbonyl)(methyl)amino)-3-(furan-2-yl)-2-methylpropyl methanesulfonate in THF (2 mL) was added and the resulting mixture was heated to reflux for 16 hours. The reaction was quenched at room temperature by addition of saturated aqueous NH4Cl solution. The mixture was neutralized to pH=7 by addition of 0.5 M KHSO4 aq solution. The aqueous layer was extracted EtOAc. The combined organic layer was washed brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/heptane, 15-50%) to give product 2.16b (50 mg, 39% yield). MS (m/z): 340 [M+1]. 1H NMR (CDCl3, 400 MHz) 7.36 (dd, J=1.96, 0.78 Hz, 1H) 6.32 (dd, J=3.33, 1.76 Hz, 1H) 6.17-6.25 (br. d., 1H) 5.08-5.21 (br. dd, 1H) 3.92 (br. s., 1H) 3.76-3.86 (m, 2H) 3.66-3.76 (m, 2H) 3.27 (br. s., 1H) 3.08 (br. s., 1H) 2.71 (s, 3H) 2.32-2.45 (m, 1H) 1.74-1.91 (m, 2H) 1.58 (s, 1H) 1.41-1.53 (m, 9H) 1.03 (d, J=6.65 Hz, 3H)

Provenance & Evidence