Hydrochloric Acid → HCID 86737310, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of nitrogen, 0.1 ml of DBU was added to a solution of 50 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxy-20-chloroprost-13-enoic acid methyl ester (prepared as described in Example 3) in 0.2 ml of toluene. The mixture was stirred at 50° C. for 1 hour, then at 70° C. for 1.5 hours and then cooled to 0° C. To the reaction mixture were added 0.5 ml of 1 N hydrochloric acid and 0.5 ml of phosphate buffer solution (pH 6.86) with cooling to 0° C. The reaction mixture was extracted quickly with diethyl ether. The extract was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on Florisil using a mixture of ethyl acetate and n-hexane (1:1) containing 0.1% of triethylamine as eluent to give 15 mg of the title compound having the following physical characteristics:

Provenance & Evidence