Hydrochloric Acid → HCID 58742350, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the compound of Example 102 (80 mg, 0.23 mmol) in acetone (15 mL) was cooled to 0° C. p-Nitrobenzoyl chloride (46 mg, 0.25 mmol) and aqueous 1N sodium hydroxide solution were then added. After the mixture was stirred at 0° C. for 1.5 hours, aqueous saturated sodium bicarbonate solution was added. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and concentrated to afford the crude p-nitrobenzoyl ester derivative. This was dissolved in dichloromethane (15 mL) and treated with aqueous 6N hydrochloric acid solution (0.038 mL). After it was cooled to −30° C., ozone was bubbled through the solution until disappearance of starting material was evident by thin layer chromatography. Oxygen was bubbled for an additional 5 minutes and then dimethylsulfide (0.5 mL) was added. The mixture was allowed to warm to room temperature overnight and was then concentrated. The residue was taken up in tetrahydrofuran (10 mL), treated with aqueous 1N sodium hydroxide solution (5 mL) and stirred at room temperature for 2 hours. Excess aqueous 1N hydrochloric acid solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate solution and brine. After drying over magnesium sulfate, evaporation provided a residue from which the title compound was isolated by chromatography on silica gel eluting with 40% ethyl acetate in hexane. Mass spectrum (m/e) 368 (M++1).

Provenance & Evidence