Reacción #81725

ord-e1717645044a464f8aa75e660cd0f8f3

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CO
methanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturais heated
  2. 2
    Temperaturaat reflux for 5 h
  3. 3
    OtroThe volatiles are then removed at reduced pressure
  4. 4
    workup.ADDITIONthe residue is diluted with water
  5. 5
    Extracciónextracted with EtOAc
  6. 6
    ExtracciónThe organic extract
  7. 7
    Lavadois washed with water and brine
  8. 8
    Otrodried
  9. 9
    Otroevaporated

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05618806uspto-grants-1997_04