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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 64736Generated: October 27, 2026

Dimethylformamide → 16beta-Ethyl-17beta-(2-hydroxy-4-methylvaleryloxy)acetoxy-4-estren-3-one

https://huagongshe.com/reaction/64736

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium HydroxideHCID 14798—
Reactant(+-)-2-Hydroxyisocaproic acidHCID 92779—
Reactant16beta-Ethyl-17beta-bromoacetoxy-4-estren-3-oneHCID 15593764—
SolventAcetoneHCID 180—
Product16beta-Ethyl-17beta-(2-hydroxy-4-methylvaleryloxy)acetoxy-4-estren-3-oneHCID 7046767096.3%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04609650
Source datasetuspto-grants-1986_09
ORD IDord-8d75143b7589477eb7b0b8c2e8274815
Source noteuspto-grants-1986_09