Reacción #812441

ord-6280d3e33d7e42d29f4bb246ba4d1112

Ecuación de reacción

aminoguanidine hydrogencarbonate

HCl

$C/C(C=O)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C$

(E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxaldehyde

→

$CC(/C=N/NC(=N)N)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C$

title compound

Rendimiento 68.3%

$CC(/C=N/NC(=N)N)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C$

(E,E)-17β-(3-Guanidinoimino-2-methyl-1-propenyl)-5β-androstane-3β,14β-diol

Rendimiento 68.3%

Reactantes

aminoguanidine hydrogencarbonate

HCl

$C/C(C=O)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C$

(E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxaldehyde

Reactivos

Ninguno

Disolventes

water

dioxane

Condiciones de reacción

Condiciones detalladas

See reaction.notes.procedure_details.

Tratamiento posterior

1
OtroAfter 3 days the mixture was evaporated to dryness under reduced pressure
2
OtroThe crude product was purified by flash chromatography (SiO2)
3
workup.ADDITIONthe fractions containing the title compound
4
Otrowere collected
5
Otroevaporated to dryness

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05705662uspto-grants-1998_01