Hydrochloric Acid → (3beta,5beta,12beta)-3,12,14-Trihydroxycard-20(22)-enolide--water (1/1)

HRID 1707945Notes

Reaction equation

HRID 1707945 reaction equation
C[C@H]1[O:7][C@@H](O[C@H]2[C@@H](O)C[C@H](O[C@H]3[C@@H](O)C[C@H]([O:24][C@@H:25]4[CH2:30][C@H:29]5[CH2:31][CH2:32][C@H:33]6[C@@:38]7([OH:48])[CH2:39][CH2:40][C@H:41]([C:42]8[CH2:47][O:46][C:44](=[O:45])[CH:43]=8)[C@@:37]7([CH3:49])[C@H:36]([OH:50])[CH2:35][C@@H:34]6[C@@:28]5([CH3:51])[CH2:27][CH2:26]4)O[C@@H]3C)O[C@@H]2C)C[C@H](O)[C@@H]1O.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH3:51][C@@:28]12[C@H:34]3[CH2:35][C@@H:36]([OH:50])[C@:37]4([CH3:49])[C@@H:41]([C:42]5[CH2:47][O:46][C:44](=[O:45])[CH:43]=5)[CH2:40][CH2:39][C@:38]4([OH:48])[C@@H:33]3[CH2:32][CH2:31][C@@H:29]1[CH2:30][C@@H:25]([OH:24])[CH2:26][CH2:27]2.[OH2:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2724385Digoxin

Product 1

HCID 16219290(3beta,5beta,12beta)-3,12,14-Trihydroxycard-20(22)-enolide--water (1/1)Yield 97.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 4.7 grams of digoxin in 300 ml of 95% aqueous ethanol containing 4.7 ml of conc. hydrochloric acid was stirred for four days with a bar magnet stirrer at ambient temperature. Crystalline sodium carbonate was added to neutralize the solution. The filtered solution was evaporated to dryness under vacuum resulting in a white semi-solid residue. This was mulled well in 50 ml of water to remove carbohydrates. The air dried product was dissolved in acetone, filtered and the solution was evaporated to dryness. The product was mulled in ethyl ether to yield 2.4 grams of white crystalline digoxigenin hydrate, m.p. 130°-140°. On HPLC in system C the product was homogeneous with a retention time of 15.2 compared with 20.7 min. for digoxin. TLC in system B gave a blue fluorescent spot at Rf 0.64 for digitoxigenin, compared with Rf 0.49 for digoxin.

Workup

  1. customThe filtered solution was evaporated to dryness under vacuum
  2. customresulting in a white semi-solid residue
  3. customto remove carbohydrates
  4. dissolutionThe air dried product was dissolved in acetone
  5. filtrationfiltered
  6. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-b8f3b66dea454eb892bcc5d6117bad82
Source dataset
uspto-grants-1994_10
Patent number
US05356881

Reaction notes

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