Reacción #354816

ord-3dc92c77d11c46c3acca2060d857e6e2

Ecuación de reacción

C[C@]12C[C@H]3O[C@H]3C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
2α,3α-epoxy-5α-androstan-11-one-17β-carboxylic acid
O=S(=O)(O)O
sulphuric acid
CCO
ethanol
O
Water
→
CCO[C@H]1C[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC[C@H](C(=O)O)[C@@]4(C)CC(=O)[C@@H]32)C[C@@H]1O
title compound
CCO[C@H]1C[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC[C@H](C(=O)O)[C@@]4(C)CC(=O)[C@@H]32)C[C@@H]1O
2β-Ethoxy-3α-hydroxy-5α-androstan-11-one-17β-carboxylic acid

Reactantes

C[C@]12C[C@H]3O[C@H]3C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
2α,3α-epoxy-5α-androstan-11-one-17β-carboxylic acid
O=S(=O)(O)O
sulphuric acid
CCO
ethanol
O
Water

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe reaction mixture extracted with chloroform
  2. 2
    LavadoThe chloroform solution was washed with water
  3. 3
    Otrodried
  4. 4
    Filtraciónfiltered
  5. 5
    Otroevaporated
  6. 6
    Otroto give a froth which
  7. 7
    Otrotriturated with chloroform/petrol
  8. 8
    FiltraciónFiltration
  9. 9
    Otroafforded the solid crude product (752 mg.) which
  10. 10
    Otroafter recrystallisation from ethanol/water

Procedimiento

A solution of 2α,3α-epoxy-5α-androstan-11-one-17β-carboxylic acid (940 mg.) and concentrated sulphuric acid (0.25 ml.) in dry ethanol (30 ml.) was stirred at room temperature for 30 minutes. Water (100 ml.) was added and the reaction mixture extracted with chloroform. The chloroform solution was washed with water, dried, filtered and evaporated to give a froth which solidified when triturated with chloroform/petrol. Filtration afforded the solid crude product (752 mg.) which, after recrystallisation from ethanol/water, afforded the pure title compound; m.p. 249°-260°; [α]D + 74°, (c 0.33).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US03943124uspto-grants-1976_03