Reacción #416835

ord-0ecd5eed1b174c2eae7bbd0d77aa42b8

Ecuación de reacción

Cl
HCl
O
water
CCOC(=O)[C@@H]1CC[C@@]2(C)[C@@H](C1)C[C@H](C(=O)OCC)[C@@H]1[C@@H]2C[C@H](O)[C@]2(C)[C@@H]([C@H](C)CC(C)C(=O)OC)CC[C@@H]12
3α,7β-diethoxycarbonyl-12α-hydroxy-23-methyl-5β-cholan-24-oic acid, methyl ester
[Na+].[OH-]
NaOH
→
CC(C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C)C(=O)O
title compound
CC(C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C)C(=O)O
3α,7β,12α-Trihydroxy-23-methyl-5β-cholan-24-oic acid

Reactantes

Cl
HCl
O
water
CCOC(=O)[C@@H]1CC[C@@]2(C)[C@@H](C1)C[C@H](C(=O)OCC)[C@@H]1[C@@H]2C[C@H](O)[C@]2(C)[C@@H]([C@H](C)CC(C)C(=O)OC)CC[C@@H]12
3α,7β-diethoxycarbonyl-12α-hydroxy-23-methyl-5β-cholan-24-oic acid, methyl ester
[Na+].[OH-]
NaOH

Reactivos

Ninguno

Disolventes

CCO.O
water ethanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónextracted with 4×40 ml of CHCl3
  2. 2
    LavadoThe organic solution was washed with NaCl-saturated water
  3. 3
    Otrodried on MgSO4

Procedimiento

The solution of 3α,7β-diethoxycarbonyl-12α-hydroxy-23-methyl-5β-cholan-24-oic acid, methyl ester (0.6 g; 0.0011 mol) in 20 ml of a water/ethanol mixture (40/60) and 3 g of NaOH was refluxed for 12 hours, then treated with 80 ml of water, acidified with concentrated HCl and extracted with 4×40 ml of CHCl3. The organic solution was washed with NaCl-saturated water and dried on MgSO4. By chromatography on silica gel, under N2 -pressure (eluent: CHCl3), 340 mg of the title compound were obtained. M.p. 151°-153° C. The structure of the compound is fully confirmed by the analytical and spectral data.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04892868uspto-grants-1990_01