Reaction #81732

ord-83c636ab3bb549998c6a6c73a0e2a87c

Reaction equation

C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@@H]2C(=O)c1ccccc1
17β-Benzoyl-estra-1,3,5(10)-triene-3-carboxylic acid
[Na+].[OH-]
sodium hydroxide
→
C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@H]2C(=O)c1ccccc1
title compound
C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@H]2C(=O)c1ccccc1
17α-Benzoyl-estra-1,3,5(10)-triene-3-carboxylic Acid

Reactants

C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@@H]2C(=O)c1ccccc1
17β-Benzoyl-estra-1,3,5(10)-triene-3-carboxylic acid
[Na+].[OH-]
sodium hydroxide

Reagents

None

Solvents

CS(C)=O
dimethyl sulfoxide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherInto a 250 ml 3-neck round bottom flask is placed
  2. 2
    TemperatureThe mixture is heated
  3. 3
    Temperatureto reflux for 3 hours

Procedure

Into a 250 ml 3-neck round bottom flask is placed 17β-Benzoyl-estra-1,3,5(10)-triene-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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05618806uspto-grants-1997_04