Dimethyl Sulfoxide → HCID 59200366, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (5.39 mL, 61.53 mmol) in dichloromethane (100 mL) was added dropwise dry DMSO (6.83 mL, 96.15 mmol) at −78° C. After 10 minutes at this temperature, a solution of benzyl 3-hydroxy-2,2-diphenylpropylcarbamate (13.9 g, 38.46 mmol) in dichloromethane (100 mL) was slowly added and stirred at −78° C. The reaction was stirred for 1 hour and triethylamine (26.8 mL, 192.3 mmol) was added and the reaction stirred at −78° C. for 10 more minutes then warmed to room 23° C. The reaction was diluted with 1N HCl and the phases were separated. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude title material (12.09 g, 87%) as an oil which was used as such in the next reaction. HPLC ret. time (Condition A): 2.093 min. LC/MS (M+H)+: 360. 1H NMR (400 MHz, CDCl3) δ ppm: 4.18 (2H, d, J=6.57 Hz), 4.98 (2H, s), 5.00 (1H, t, J=5.81 Hz), 7.17-7.42 (15H, 2 m), 9.90 (1H, s).

Provenance & Evidence