Acetic Acid → (13E)-(11alpha,15S)-6,9-Dioxo-11,15-dihydroxyprost-13-enoic acid methyl ester

Temperature

45 °C

To a solution of 480 mg of (13E)-(11α,15S)-6,9-dioxo-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 1) in 1 ml of tetrahydrofuran was added 3 ml of 65% (v/v) aqueous acetic acid and the mixture was stirred at 45° C. for 3 hours. The reaction mixture was diluted with 16 ml of water and extracted with a mixture of ethyl acetate and n-hexane (1:1). 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 ethyl acetate and n-hexane (1:1) as eluent to give 177 mg of the title compound having the following physical characteristics:

1. extractionextracted with a mixture of ethyl acetate and n-hexane (1:1)
2. washThe extract was washed with water
3. dry with materialan aqueous solution of sodium bicarbonate and an 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 ethyl acetate and n-hexane (1:1) as eluent

ORD record

ord-db1754b64c774c43b8aeb679e4c57478

Source dataset

uspto-grants-1980_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04215142