HuagongsheHuagongshe Chemistry Print Report · For research reference only
(8S,11R,13S,14S,17S)-17-hydroxy-11-[4-((RS)-1-hydroxyethyl)phenyl]-1 3-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one → (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-{4-[(RS)-1-(2-methylbenzothiazol-5-ylmethoxy)ethyl]phenyl}-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (8S,11R,13S,14S,17S)-17-hydroxy-11-[4-((RS)-1-hydroxyethyl)phenyl]-1 3-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one | HCID 18346565 | — |
| Reactant | 5-Bromomethyl-2-methylbenzothiazole | HCID 21190757 | — |
| Product | (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-{4-[(RS)-1-(2-methylbenzothiazol-5-ylmethoxy)ethyl]phenyl}-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one | HCID 50915135 | 24% |
Reaction Steps
In analogy to Example 2, 500 mg (0.98 mmol) of (8S,11R,13S,14S,17S)-17-hydroxy-11-[4-((RS)-1-hydroxyethyl)phenyl]-13-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one were converted using 5-bromomethyl-2-methylbenzothiazole and, after workup and purification, 157 mg (24%) of the title compound were isolated as a colourless foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096640B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-1be6cf4b0df04b098f35f9bb8a072eea |
| Source note | uspto-grants-2015_08 |