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3-beta-acetoxy-14-hydroxy-5-beta,14-beta-card-20(22)-enolide synthesis

9synthesis methods
-

Yield:808-19-5 100%

Reaction Conditions:

with pyridine;dmap at 20 - 30;Inert atmosphere;

Steps:

1; 2 Digitoxigenin to 3-acetyl-digitoxigenin

To a solution of 25 grams of digitoxigenin in 118ml of pyridine under Argon atmosphere, 41mg of DMAP and 33.1ml of acetic anhydride were added, maintaining the temperature below 30°C. After stirring at room temperature for 20h, the solvent was removed under reduced pressure (co-evaporating with toluene). The residue was taken up with 480ml of water and stirred at room temperature for 1h. The resulting solid was collected by filtration, washed with 240ml of water and dried under vacuum, giving 28.04g (quantitative yield) of product 1 as pale-yellow solid, used in the next step without any further purification.

References:

EP3599243,2020,A1 Location in patent:Paragraph 0112-0115; 0132-0134