Dimethylformamide → 16beta-Ethyl-17beta-(3-methylbutyryl)oxyacetoxy-4-estren-3-one

HRID 64735Notes

Reaction equation

HRID 64735 reaction equation
[C:1]([O-:7])(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[Na+].[CH2:9]([C@H:11]1[CH2:16][C@H:15]2[C@H:17]3[C@H:26]([CH2:27][CH2:28][C@:13]2([CH3:14])[C@H:12]1[O:30][C:31](=[O:34])[CH2:32]Br)[C@@H:25]1[C:20](=[CH:21][C:22](=[O:29])[CH2:23][CH2:24]1)[CH2:19][CH2:18]3)[CH3:10].CN(C=O)C>O.CC(C)=O>[CH2:9]([C@H:11]1[CH2:16][C@H:15]2[C@H:17]3[C@H:26]([CH2:27][CH2:28][C@:13]2([CH3:14])[C@H:12]1[O:30][C:31](=[O:34])[CH2:32][O:6][C:1](=[O:7])[CH2:2][CH:3]([CH3:5])[CH3:4])[C@@H:25]1[C:20](=[CH:21][C:22](=[O:29])[CH2:23][CH2:24]1)[CH2:19][CH2:18]3)[CH3:10]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-oneHCID 23673832Sodium Isovalerate

Product 1

HCID 7046730816beta-Ethyl-17beta-(3-methylbutyryl)oxyacetoxy-4-estren-3-oneYield 87.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

In a mixture of 2 ml of water and 2 ml of acetone is dissolved 0.26 g of sodium isovalerate, and 0.45 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 10 ml of DMF are added to the above solution. The mixture is refluxed for 6 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is then subjected to column chromatography. Following passage of 100 ml of diisopropyl ether-n-hexane (2:8), elution is carried out with 400 ml of a 1:1 mixture of the same solvents. The elutate is evaporated under reduced pressure to remove the solvent, giving 0.415 g of the above-identified compound as a colorless viscous oil.

Workup

  1. additionare added to the above solution
  2. temperatureThe mixture is refluxed for 6 hours
  3. additiontreated in the same manner as Example 26
  4. washpassage of 100 ml of diisopropyl ether-n-hexane (2:8), elution
  5. additionis carried out with 400 ml of a 1:1 mixture of the same solvents
  6. customThe elutate is evaporated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-d51e0e4020a2488db56dcccc51125eed
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

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