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 | — |
| Reactant | Acetic water tetrahydrofuran | HCID 131711181 | — |
| 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/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 | US04105792 |
| Source dataset | uspto-grants-1978_08 |
| ORD ID | ord-a09b0eed64cf44ef93929ddc577c36f8 |
| Source note | uspto-grants-1978_08 |