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

HRID 64730
Notes
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Reaction equation

HRID 64730 reaction equation
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24]Br)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].CN(C=O)C.[CH:32]1([CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CC(C)=O.[OH-].[Na+]>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][O:42][C:40](=[O:41])[CH2:39][CH2:38][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 69702Cyclohexanepropanoic acidHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046767116beta-Ethyl-17beta-(3-cyclohexylpropionyl)oxyacetoxy-4-estren-3-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent
HCID 14798
Sodium Hydroxide
Solvent

Procedure

In 20 ml of acetone is dissolved 1.0 ml of cyclohexanepropionic acid, and 3.0 ml of 2N-NaOH is added, followed by addition of 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 20 ml of DMF. The mixture is refluxed for 8 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is chromatographed on a silica gel column. Following passage of 200 ml of n-hexane-diisopropyl ether (3:7), elution is carried out with 800 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.21 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for 8 hours
  3. additiontreated in the same manner as Example 26
  4. customThe reaction mixture is chromatographed on a silica gel column
  5. washpassage of 200 ml of n-hexane-diisopropyl ether (3:7), elution
  6. additionis carried out with 800 ml of a 1:1 mixture of the same solvents
  7. customThe eluate is evaporated under reduced pressure
  8. customto remove the solvent

Sources & evidence

ORD record
ord-63038de424534fef9fb36a0e4480c1ce
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04609650

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes