HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 16beta-Ethyl-17beta-(2-hydroxy-4-methylvaleryloxy)acetoxy-4-estren-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (+-)-2-Hydroxyisocaproic acid | HCID 92779 | — |
| Reactant | 16beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one | HCID 15593764 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 16beta-Ethyl-17beta-(2-hydroxy-4-methylvaleryloxy)acetoxy-4-estren-3-one | HCID 70467670 | 96.3% |
Reaction Steps
In 2.0 ml of acetone is dissolved 0.26 g of leucic acid, and 1.0 ml of 2N-NaOH is added, followed by addition of 0.44 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 15 ml of DMF. The mixture is refluxed for 3 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is then subjected to column chromatography. Following passage of 50 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 200 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.475 g of the above-identified compound as a viscous oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04609650 |
| Source dataset | uspto-grants-1986_09 |
| ORD ID | ord-8d75143b7589477eb7b0b8c2e8274815 |
| Source note | uspto-grants-1986_09 |