Methanesulfonyl chloride → HCID 70229960, compound

Participants

Reaction Conditions

Reaction Steps

319 mg of methane sulfonic acid chloride is added at 0° C. to a solution of 1.00 g of (4Z,13E)-(9S,11R,15R)-9-hydroxy-16,16-dimethyl-11,15-bis-(tetrahydropyran-2-yloxy)-4,13-prostadienoic acid methyl ester in 10 ml of pyridine. It is stirred for 4 hours at 20° C. and the solution is added to a suspension of 9.99 g of tetrabutylammonium chloride in 10 ml of toluene. After 15-hours stirring at 0° C., it is stirred for another 7 hours at 40° C. Then it is added to 100 ml of ice water and extracted three times with 50 ml each of ether. After the organic phase is washed twice with 20 ml of brine, dried over MgSO4 and is concentrated by evaporation in a vacuum a-residue is obtained which is chromatographed on silica gel with hexane/0-40% ether. 839 mg of oily (4Z,13E)-(9R,11R,15R)-9-chioro-16,16-dimethyl-11,15-bis(tetrahydropyran-2-yloxy)-4,13-prostaqienoic acid methyl ester is obtained. For cleavage of the protecting groups, the resulting ester is stirred with 31 ml of a mixture of acetic acid/water/ tetrahydrofuran (65/35/10) for 24 hours at 20° C. After addition of toluene and concentration of the solution by evaporation in a vacuum the residue is chromatographed on silica gel. With toluene/0-10% isopropanol as eluant, 326 mg of the title compound is obtained as colorless oil.

Provenance & Evidence