Hydrochloric Acid → Gitoxigenin

HRID 1707944Notes

Reaction equation

HRID 1707944 reaction equation
C[C@H]1O[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:49])[CH2:39][C@H:40]([OH:48])[C@H:41]([C:42]8[CH2:47][O:46][C:44](=[O:45])[CH:43]=8)[C@@:37]7([CH3:50])[CH2:36][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>[CH3:51][C@@:28]12[C@H:34]3[CH2:35][CH2:36][C@:37]4([CH3:50])[C@@H:41]([C:42]5[CH2:47][O:46][C:44](=[O:45])[CH:43]=5)[C@@H:40]([OH:48])[CH2:39][C@:38]4([OH:49])[C@@H:33]3[CH2:32][CH2:31][C@@H:29]1[CH2:30][C@@H:25]([OH:24])[CH2:26][CH2:27]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 91540Gitoxin

Product 1

HCID 348482GitoxigeninYield 93.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4.7 grams of gitoxin in 300 ml of ethanol containing 4.7 ml of conc. hydrochloric acid was stirred for three days, warmed gently for ten hours then stirred for another day at room temperature. The acidic solution was neutralized by the addition of solid sodium carbonate, then filtered to yield a clear colorless solution. The solvent was removed on a rotary evaporator and the residue was mulled in water to remove carbohydrate hydrolysis products. The residue was extracted into a solution of 100 ml of ethyl acetate and 30 ml of acetone, then filtered. A product crystallized as the solvent was removed under vacuum. The residue was mulled in ethyl ether to yield 2.2 grams of white crystalline gitoxigenin. On HPLC using system C as in Example 1. gitoxigenin had a retention time of 13.9 minutes, compared to a starting material reference gitoxin at 20.7 minutes. On TLC using system B gitoxigenin showed a blue fluorescent spot at Rf 0.69, compared to gitoxin at Rf 0.23. The product was about 95% pure gitoxigenin.

Workup

  1. temperaturewarmed gently for ten hours
  2. stirringthen stirred for another day at room temperature
  3. filtrationfiltered
  4. customto yield a clear colorless solution
  5. customThe solvent was removed on a rotary evaporator
  6. customto remove
  7. customcarbohydrate hydrolysis products
  8. extractionThe residue was extracted into a solution of 100 ml of ethyl acetate and 30 ml of acetone
  9. filtrationfiltered
  10. customA product crystallized as the solvent
  11. customwas removed under vacuum

Sources & evidence

ORD record
ord-41549b0b1b8e4a16b8d5775274d30998
Source dataset
uspto-grants-1994_10
Patent number
US05356881

Reaction notes

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