HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 2-((10S,13S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Hydrocortisone Acetate | HCID 5744 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 2-((10S,13S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate | HCID 13037657 | — |
Reaction Steps
The title compound can be synthesized from hydrocortisone acetate according to the procedure disclosed in EP 0097328.405 g (1 mol) of hydrocortisone acetate is added to a mixture of 2 liters of N,N-dimethylformamide and 350 ml of pyridine, and with stirring at room temperature, 260 g of methanesulfonyl chloride is added. The reaction mixture is heated, maintained at 80 to 85° C. for 1 hour, and then cooled to room temperature. Methanol (7 liters) is added. The precipitated crystals are separated by filtration, washed with methanol and water, and dried under reduced pressure to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08207151B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-97da3a34fedc484baa30d0411039bf73 |
| Source note | uspto-grants-2012_06 |