Hydrochloric Acid → HCID 86737309, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of nitrogen, a solution of 116 mg of (13E)-(5RS,6RS,9α,11α,15S,16RS)-5-iodo-6,9-epoxy-11,15-dihydroxy-16-methyl-20-chloroprost-13-enoic acid methyl ester (prepared as described in Example 1) and 0.4 ml of 1,5-diazabicyclo[5,4,0]undecene-5 (DBU) was stirred at room temperature for 18 hours, and then cooled to 0° C. To the reaction mixture were added 2 ml of 1 N hydrochloric acid and 2 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 magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on Florisil (an activated magnesium silicate: "Florisil" is a registered Trade Mark of Florin Co.) using a mixture of ethyl acetate and n-hexane (1:1) containing 0.1% of triethylamine as eluent to give 52 mg of the title compound having the following physical characteristics:

Provenance & Evidence