Dimethyl Sulfoxide → HCID 70067124, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (87 μl, 1.24 mmol, 2.0 eq) dry dimethylsulfoxide in 3 ml of dry CH2Cl2 at -65° C. was added (0.46 ml, 0.927 mmol, 1.5 eq) of 2.0M oxalyl chloride in CH2 Cl2. The mixture was stirred at ca. -60° C. for 15 minutes, then a solution of (310 mg, 0.618 mmol, 1.0 eq) 2-[[3-(bicyclo[2.2.1]hept-2-yloxy)-4-methoxyphenyl]hydroxy-methyl]-4-(phenylmethyl)-2H-1,4-benzothiazin-3(4H)-one in 10 ml dry CH2Cl2 was added dropwise at -65° C. The mixture was allowed to warm to -30° C. over 1 hour, then cooled to -78° C. and (0.43 ml, 3.09 mmol, 5.0 eq) triethylamine was added to the mixture. The mixture was stirred at room temperature for 1 hour then diluted with 400 ml ethyl acetate, washed twice with H2O, once with brine, dried over MgSO4, and concentrated to give 0.3 g of an oil. Silica gel chromatography eluting with 10% ethyl acetate-hexane gave 120 mg of a yellow oil, which was recrystallized from ether-hexane to yield 55 mg, 18%, of a yellow solid. M.P.: 135°-137° C. Elemental Analysis Calc'd for C30H29NO3S: Calc'd: C, 74.51; H, 6.04; N, 2.90. Found: C, 74.53; H, 5.48; N, 2.88.

Provenance & Evidence