Dimethyl Sulfoxide → HCID 59161024, compound

Participants

Reaction Conditions

Reaction Steps

553.7 mg (4.36 mmol) of oxalyl chloride are dissolved in 25 ml of dichloromethane and cooled to −78° C. 681.6 mg (8.72 mmol) of dimethyl sulfoxide are added slowly. A solution of 1.20 g (2.91 mmol) of the compound from Example 4A in 10 ml of dichloromethane is then added dropwise. The mixture is stirred at −78° C. for 1 h. 2.0 ml (14.54 mmol) of triethylamine are then added, and the mixture is allowed to warm to RT over a period of 1 h. The mixture is then added to 20 ml of a 1:1 mixture of saturated aqueous sodium bicarbonate solution and ethyl acetate. After separation of the phases the aqueous phase is extracted two more times with in each case 10 ml of ethyl acetate. The combined organic phases are freed from the solvent on a rotary evaporator. The residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→5:1).

Provenance & Evidence