Hydrogen Peroxide → (4E,13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-4,13-dienoic acid methyl ester

To a solution of 560 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-phenylseleno-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 6) in a mixture of 6 ml of ethyl acetate and 3 ml of tetrahydrofuran was added 0.5 ml of 30% hydrogen peroxide and 100 mg of sodium bicarbonate, and the reaction mixture was then stirred for one hour. Afterwards it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium carbonate, water 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 benzene and ethyl acetate (6:1) as eluent to give 380 mg of the title compound having the following physical characteristics:

1. extractionAfterwards it was extracted with ethyl acetate
2. washThe extract was washed with an aqueous solution of sodium carbonate, water
3. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by column chromatography on silica gel using
6. additiona mixture of benzene and ethyl acetate (6:1) as eluent

ORD 기록

ord-0720ed4f739e421883eb9a254718f125

출처 데이터셋

uspto-grants-1983_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04399147