Hydrogen Peroxide → HCID 86650567, compound

Participants

Reaction Steps

3-(phenylsulfinyl)-4,5-dihydroisoxazole I-249a and I-249b were prepared by the oxidation of racemic 3-(phenylthio)-4,5-dihydroisoxazole I-248. 3-(Phenylthio)-4,5-dihydroisoxazole I-248 (1.0 equiv) was dissolved in ethanol (0.15 M) followed by the addition of excess hydrogen peroxide in water (30% by weight, >50 equiv) and 1N HCl (0.29 M). The reaction was stirred at room temperature for 14 h after which it was transferred to a separatory funnel with excess water and methylene chloride. The water layer was extracted with methylene chloride (1×), dried over magnesium sulfate, and concentrated to provide crude product that was recrystallized from hexanes to provide the desired racemic 3-(phenylsulfinyl)-4,5-dihydroisoxazole I-249. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=355.5 m/z. Activity: C

Provenance & Evidence