Dimethyl Sulfoxide → HCID 70159661, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (13.0 mL, 150 mmol) in dichloromethane (300 mL) at −78° C. was treated dropwise with DMSO (14.6 mL, 205 mmol), stirred for 10 minutes, treated with the product from Example 1C (46 g, 100 mmol) in dichloromethane (50 mL), stirred for 30 minutes, treated with triethylamine (55 mL, 400 mmol), warmed to 0° C. over 30 minutes, quenched with 10% NaHCO3, and extracted with diethyl ether. The organic layer was washed with 10% NaHSO4, 10% NaHCO3 and brine, dried (Na2SO4) and concentrated. The crude product was filtered through a plug of silica gel with 7:3 hexane/ethyl acetate to provide the title compound. 1H NMR (300 MHz, CDCl3) δ1.52 (d, 3H), 4.00 (d, 1H), 4.22 (d, 1H), 4.30 (d, 0.5H), 4.45 (d, 0.5H), 4.57 (d, 0.5H), 4.71 (d, 0.5H), 5.05-5.30 (m, 2H), 5.51 (q, 0.5H), 5.68 (q, 0.5H), 6.62 (d, 0.5H), 6.92 (d, 0.5H), 7.05 (t, 1H), 7.20-7.42 (m, 10H), 7.50 (t, 1H), 7.88 (d, 1H).

Provenance & Evidence