Hydrochloric Acid → HCID 22867510, compound

Participants

Reaction Steps

A solution of 13.5 μL (0.170 mmol) of methanesulfonyl chloride in 300 μL of methylene chloride was slowly added to a cold (0° C.) solution of 80 mg (0.23 mmol) of the subtitled intermediate of Preparation 1D and 32 μL (0.23 mmol) of triethylamine in 0.6 mL of methylene chloride. The reaction mixture was warmed to room temperature, allowed-to react for 15 minutes and then poured into 50 mL of a 3:2 mixture of diethyl ether and 0.1N hydrochloric acid. The resulting layers were separated and the organic layer was washed with a half-saturated sodium bicarbonate solution and then reduced to dryness under reduced pressure to provide a foam. This foam was purified using column chromatography (eluted with a 1:2 ethyl acetate/methylene chloride solution). The fractions containing the desired product were combined and reduced to dryness under reduced pressure to provide 100 mg of a 60:40 mixture of the desired subtitled intermediate and the starting material, 1,6-diphenyl-2(S),5(S)-diazido-3(R),4(R)-dihydroxyhexane.

Provenance & Evidence