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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

HRID 725259
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 725259
C(=O)(O)O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].Cl.[OH:11][C@H:12]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@:18]3([OH:36])[CH2:19][CH2:20][C@@H:21]2/[CH:22]=[C:23](\[CH3:26])/[CH:24]=O)[CH2:13]1>O.O1CCOCC1>[NH:6](/[N:5]=[CH:24]/[C:23](/[CH3:26])=[CH:22]/[C@H:21]1[CH2:20][CH2:19][C@:18]2([OH:36])[C@H:17]3[C@H:30]([CH2:29][CH2:28][C@:27]12[CH3:35])[C@:31]1([CH3:34])[C@@H:14]([CH2:13][C@@H:12]([OH:11])[CH2:33][CH2:32]1)[CH2:15][CH2:16]3)[C:7]([NH2:9])=[NH:8]
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Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 10666253(E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxaldehydeHCID 178513185HCID 178513185, Verbindung

Produkt 1

HCID 1765375471-[(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]guanidineAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. customAfter 3 days the mixture was evaporated to dryness under reduced pressure
  2. customThe crude product was purified by flash chromatography (SiO2)
  3. additionthe fractions containing the title compound
  4. customwere collected
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6280d3e33d7e42d29f4bb246ba4d1112
Quelldatensatz
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05705662

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