Reaction #81724

ord-310ecfb86a4b40d589cf751e84ec977e

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
    Temperaturewas heated
  2. 2
    Temperatureat reflux for 5 h
  3. 3
    OtherThe volatiles were then removed at reduced pressure
  4. 4
    workup.ADDITIONthe residue was diluted with water
  5. 5
    Extractionextracted with EtOAc
  6. 6
    ExtractionThe organic extract
  7. 7
    Washwas washed with water and brine
  8. 8
    Otherdried
  9. 9
    Otherevaporated to dryness

Procedure

A mixture of methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate (60 mg, 0.15 mmol), K2CO3 (60 mg, 0.44 mmol), water (1 mL), and methanol (9 mL) was heated at reflux for 5 h. The volatiles were then removed at reduced pressure and the residue was diluted with water, acidified with dilute aqueous HCl, and extracted with EtOAc. The organic extract was washed with water and brine, dried, and evaporated to dryness. Trituration of the residue with acetone and methanol provided the title compound as a white solid, mp 240°-243° C.

Source

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