Hydrochloric Acid → HCID 67922906, compound

HRID 329653Notes

Reaction equation

HRID 329653 reaction equation
C(OC([C@@H:6]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:8]([CH2:9][C@H:10](C(OCC)=O)[C@@H:11]3[C@@H:28]2[CH2:27][C@H:26]([OH:33])[C@@:25]2([CH3:34])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:24])[CH2:17][CH:18]([CH3:23])[C:19]([O:21]C)=[O:20])[CH2:7]1)=O)C.[OH-:40].[Na+].[OH2:42].Cl>O.C(O)C>[OH:40][C@@H:6]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:8]([CH2:9][C@H:10]([OH:42])[C@@H:11]3[C@@H:28]2[CH2:27][C@H:26]([OH:33])[C@@:25]2([CH3:34])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:24])[CH2:17][CH:18]([CH3:23])[C:19]([OH:21])=[O:20])[CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86743651HCID 86743651, compound

Product 1

HCID 67922906HCID 67922906, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

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.

Workup

  1. extractionextracted with 4×40 ml of CHCl3
  2. washThe organic solution was washed with NaCl-saturated water
  3. customdried on MgSO4

Sources & evidence

ORD record
ord-0ecd5eed1b174c2eae7bbd0d77aa42b8
Source dataset
uspto-grants-1990_01
Patent number
US04892868

Reaction notes

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