Reaction #81725

ord-e1717645044a464f8aa75e660cd0f8f3

Reaction equation

COC(=O)c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)c3ccccc3)CC[C@@H]12
methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water
→
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
17β-Benzoyl-estra-1,3,5(10)-triene-3-carboxylic Acid

Reactants

COC(=O)c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)c3ccccc3)CC[C@@H]12
methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureis heated
  2. 2
    Temperatureat reflux for 5 h
  3. 3
    OtherThe volatiles are then removed at reduced pressure
  4. 4
    workup.ADDITIONthe residue is diluted with water
  5. 5
    Extractionextracted with EtOAc
  6. 6
    ExtractionThe organic extract
  7. 7
    Washis washed with water and brine
  8. 8
    Otherdried
  9. 9
    Otherevaporated

Procedure

A mixture of methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate, K2CO3, water and methanol is heated at reflux for 5 h. The volatiles are then removed at reduced pressure and the residue is diluted with water, acidified with dilute aqueous HCl, and extracted with EtOAc. The organic extract is washed with water and brine, dried, and evaporated to yield the title compound.

Source

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