Hydrochloric Acid → 1-[(E)-[(E)-3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2-methylprop-2-enylidene]amino]guanidine

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Reaction Steps

A mixture of 0.50 g of aminoguanidine hydrogencarbonate in 10 ml of water and 30 ml of dioxane was made acid to pH 3 with 3N HCl. A solution of 0.95 g of (E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxaldehyde (Prepn. 1) in 10 ml of dioxane was added at room temperature. After 3 days the mixture was evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 80/20/3 as the eluant: the fractions containing the title compound were collected and evaporated to dryness. The residue was ground with diethyl ether and ethanol to give 0.75 g of the title compound (I-aa) as a white solid.

Provenance & Evidence