Sodium Thiosulfate → tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(heptane-1-sulfonyl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-heptylsulfanyl-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate (No. 6804240; 50.9 mg, 0.0709 mmol) was dissolved in dichloromethane (3.4 mL), and the mixture was cooled to 0° C. mCPBA (72% content, 34.0 mg, 0.142 mmol) was added, and the mixture was stirred at 0° C. for 30 minutes. After completing the reaction, the progress of the reaction was stopped by adding an aqueous solution of 10% sodium thiosulfate, and the mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure to obtain 56.1 mg of tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(heptane-1-sulfonyl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate (No. 6804464; ESI (LC/MS positive mode) m/z 750 (M+H); Rt 2.15 min.).

Provenance & Evidence