Methyl iodide → HCID 178448838, compound

Participants

Reaction Steps

To a solution of Intermediate B (142 mg, 0.318 mmol) in dry THF (3 mL) was added a solution of butyl isothiocyanate (45.7 mg, 0.397 mmol) in dry THF (1 mL). The mixture was stirred at room temperature for 16 h. Solvents were evaporated under reduced pressure. The residue was dissolved in acetone (3 mL). MeI (90 mg, 0.64 mmol) was added. The mixture was stirred at room temperature for 5 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 (87.2 mg, 52%) as a syrup. 1H NMR (400 MHz, CDCl3) δ 7.38-7.26 (m, 15H), 4.83 (d, J=11.5 Hz, 1H), 4.80-4.76 (m, 1H), 4.77 (d, J=11.3 Hz, 1H), 4.69 (d, J=11.5 Hz, 1H), 4.46 (d, J=11.2 Hz, 1H), 4.45 (s, 2H), 4.05 (dd, J=7.9, 4.4 Hz, 1H), 3.64 (t, J=5.9 Hz, 1H), 3.56 (dd, J=9.0, 4.2 Hz, 1H), 3.52-3.46 (m, 2H), 3.25-3.11 (m, 2H), 2.18 (dt, J=14.8, 3.4 Hz, 1H), 2.05-1.98 (m, 1H), 1.88 (ddd, J=15.1, 12.1, 3.7 Hz, 1H), 1.53-1.46 (m, 2H), 1.38-1.28 (m, 2H), 0.90 (t, J=7.3 Hz, 3H).

Provenance & Evidence