Hydrochloric Acid → HCID 70575767, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of nitrogen, a solution of 2.233 g of (13E)-(5RS,6RS,9α,11α,15S,16S)-5-bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)-16-methylprost-13-enoic acid methyl ester [prepared as described in Reference Example 1(a)] and 7.4 ml of DBU was stirred at 70° C. for 3 hours, and then cooled to 0° C. To the reaction mixture were added 37 ml of 1 N hydrochloric acid and 37 ml of phosphate buffer solution (pH 6.68) with cooling to 0° C. The reaction mixture was extracted quickly with diethyl ether. The extract was dried over magnesium sulphate and concentrated under reduced pressure to give an oily product. To a solution of the oily product thus obtained in 40 ml of tetrahydrofuran were added dropwise 4 ml of water and 4 ml of 65% (v/v) aqueous acetic acid and the mixture was stirred at room temperature for 2 hours and then extracted with ethyl acetate. The extract was washed with water, an aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:1) as eluent to give 1.323 g of the title compound having the following physical characteristics:

Provenance & Evidence