HuagongsheHuagongshe Chemistry Print Report · For research reference only
(5Z,13E)-(8R,11R,12R,15S)-1-(N-methylcarbamoyloxy)-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-9-one → (5Z,13E)-(8R,11R,12R,15S)-1-(N-Methylcarbamoyloxy)-11,15-dihydroxy-5,13-prostadien-9-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (5Z,13E)-(8R,11R,12R,15S)-1-(N-methylcarbamoyloxy)-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-9-one | HCID 70567581 | — |
| Solvent | AcOH THF water | HCID 21877175 | — |
| Product | (5Z,13E)-(8R,11R,12R,15S)-1-(N-Methylcarbamoyloxy)-11,15-dihydroxy-5,13-prostadien-9-one | HCID 70566919 | — |
Reaction Steps
At 40°, 300 mg. of (5Z,13E)-(8R,11R,12R,15S)-1-(N-methylcarbamoyloxy)-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-9-one was agitated with 9 ml. of a mixture of glacial acetic acid/water/tetrahydrofuran (65/35/10) for 6 hours. The mixture was then evaporated to dryness under vacuum. After purifying the residue by chromatography on silica gel (ether/ethyl acetate 7+3), 145 mg. of the title compound was obtained as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04159343 |
| Source dataset | uspto-grants-1979_06 |
| ORD ID | ord-c14f7547fdb64b1bbd8c1ff53db3528a |
| Source note | uspto-grants-1979_06 |