Sodium Hydroxide → HCID 54160510, compound

HRID 1684568Notes

Reaction equation

HRID 1684568 reaction equation
[CH2:1]([C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:12]12[CH3:13])[C@:25]1([CH3:26])[C:20]([CH:21]=[C:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24]1)=[CH:19][CH2:18]3)=[O:10])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>CS(C)=O>[CH2:1]([C:9]([C@@H:11]1[CH2:16][CH2:15][C@H:14]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:12]12[CH3:13])[C@:25]1([CH3:26])[C:20]([CH:21]=[C:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24]1)=[CH:19][CH2:18]3)=[O:10])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11026423(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3-phenylpropanoyl)-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid

Product 1

HCID 54160510HCID 54160510, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Into a 250 mL 3-neck round bottom flask is placed 17β-(phenethylcarbonyl)-androsta-3,5-diene-3-carboxylic acid and an excess of sodium hydroxide. To the flask is added dimethyl sulfoxide as a solvent. The mixture is heated to reflux for 3 hours. Standard workup followed by isolation by preparative HPLC yields title compound.

Workup

  1. customInto a 250 mL 3-neck round bottom flask is placed
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 3 hours

Sources & evidence

ORD record
ord-285726ad206d4758b4ff5452085d0e1f
Source dataset
uspto-grants-1997_06
Patent number
US05641765

Reaction notes

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