Oxygen → 12,14-Dihydroxy-3-oxocard-20(22)-enolide

HRID 1455858Notes

Reaction equation

HRID 1455858 reaction equation
[CH3:1][C@@:2]12[C@H:11]3[CH2:12][C@@H:13]([OH:27])[C@:14]4([CH3:26])[C@@H:18]([C:19]5[CH2:24][O:23][C:21](=[O:22])[CH:20]=5)[CH2:17][CH2:16][C@:15]4([OH:25])[C@@H:10]3[CH2:9][CH2:8][C@@H:7]1[CH2:6][C@@H:5]([OH:28])[CH2:4][CH2:3]2.O=O>O.CC(C)=O.[Pt]>[CH3:1][C@@:2]12[CH:11]3[CH2:12][C@@H:13]([OH:27])[C@:14]4([CH3:26])[C@@H:18]([C:19]5[CH2:24][O:23][C:21](=[O:22])[CH:20]=5)[CH2:17][CH2:16][C@:15]4([OH:25])[CH:10]3[CH2:9][CH2:8][C@@H:7]1[CH2:6][C:5](=[O:28])[CH2:4][CH2:3]2

Participants

6

Reactant 2

HCID 977OxygenHCID 15478Digoxigenin

Product 1

HCID 2050312,14-Dihydroxy-3-oxocard-20(22)-enolideYield 101.5%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Platinum IV oxide (0.5 g) was added to 1.0 g of Digoxigenin and dissolved in 100 mls of water and 150 mls of acetone. The mixture was pressurized to 2 atmospheres of oxygen and shaken for catalyst was filtered off, and the solvent stripped off leaving 1.01 g of white solid. This was dissolved in 100 mls of methylene chloride and extracted with 70 mls of water. The water was back-washed with two volumes of 50 mls of methylene chloride. The organic fractions were collected, dried with anhydrous sodium sulfate and the solvent was stripped off leaving 0.75 g of white solid.

Workup

  1. filtrationwas filtered off

Sources & evidence

ORD record
ord-60917a74a962497696e42c7766135847
Source dataset
uspto-grants-1998_12
Patent number
US05843634

Reaction notes

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