Calcium Carbonate → HCID 22810249, compound

Participants

Reaction Steps

A solution of 480 mg. of (5Z,13E)-(9S,11R,15S)-9,11,15-trihydroxy-19-methyl-5,13,18-prostatrienoic acid methyl ester (prepared according to DOS No. 2,635,985) and 530 mg. of mercury(II) acetate in 20 ml. of tetrahydrofuran is stirred with 200 mg. of pulverized calcium carbonate for 48 hours at 25°, and then combined in succession at 0° with 8 ml. of 1 N sodium hydroxide solution and a solution of 200 mg. of sodium borohydride in 8 ml. of 1 N sodium hydroxide solution. The mixture is stirred for 10 minutes and poured on 100 ml. of citrate buffer (pH 4), whereafter it is extracted three times with respectively 50 ml. of methylene chloride. The extract is shaken with sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated under vacuum. The residue shows, in the thin-layer chromatogram in the system ether/dioxane (9+1), two spots which are more nonpolar as compared to the starting material. For purposes of purification, the product is chromatographed on silica gel with the use of a hexane/ethyl acetate gradient, thus obtaining 100 mg. of the nonpolar isomer and 210 mg. of the polar isomer, both in the form of oils.

Provenance & Evidence