Methyl iodide → HCID 178463382, compound

Participants

Reaction Steps

To a solution of Intermediate B (173 mg, 0.387 mmol) in dry THF (5 mL) was added a solution of ethyl isothiocyanate (42 mg, 0.48 mmol) in dry THF (3 mL). The mixture was stirred at room temperature for 24 h. Solvents were evaporated under reduced pressure. The residue was dissolved in acetone (3 mL). MeI (110 mg, 0.774 mmol) was added. The mixture was stirred at room temperature for 9 h. Satd. aqueous NaHCO3 (2 mL) was added and stirred at room temperature for 10 min. The mixture was further diluted with satd. aqueous NaHCO3 (20 mL), extracted with EtOAc (2×15 mL). The combined extracts were washed with brine and dried over Na2SO4. Solvents were evaporated under reduced pressure. The crude product was purified by silica gel column chromatography, eluted with 96:3:1 EtOAc-MeOH—NH4OH (28% aqueous) to give the aminooxazoline (181 mg, 94%) as a syrup. 1H NMR (400 MHz, CDCl3) δ 7.36-7.25 (m, 15H), 4.88-4.85 (m, 1H), 4.78 (d, J=11.8 Hz, 1H), 4.76 (d, J=11.8 Hz, 1H), 4.66 (d, J=11.3 Hz, 1H), 4.46 (d, J=11.3 Hz, 1H), 4.45 (s, 2H), 4.07 (dd, J=8.0, 5.1 Hz, 1H), 3.67 (t, J=5.7 Hz, 1H), 3.55-3.51 (m, 2H), 3.46 (dd, J=9.0, 4.2 Hz, 1H), 3.29-3.15 (m, 2H), 2.20 (dt, J=14.9, 3.7 Hz, 1H), 2.07-2.00 (m, 1H), 1.89 (ddd, J=15.2, 11.9, 3.6 Hz, 1H); MS, m/z=500 (M+1).

Provenance & Evidence