3beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehyde → HCID 178483809, compound

HRID 1735736Notes

Reaction equation

HRID 1735736 reaction equation
I.[NH2:2][NH:3][C:4]([NH:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])=[NH:5].[OH:12][C@H:13]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@H:15]([CH2:16][CH2:17][C@@H:18]3[C@@H:27]2[CH2:26][CH2:25][C@@:23]2([CH3:24])[C@:19]3([OH:34])[CH2:20][CH2:21][C@@H:22]2[CH:32]=O)[CH2:14]1>Cl.O1CCOCC1>[CH3:10][N:9]([CH3:11])[CH2:8][CH2:7][NH:6][C:4](=[NH:5])[NH:3]/[N:2]=[CH:32]/[C@H:22]1[CH2:21][CH2:20][C@:19]2([OH:34])[C@H:18]3[C@H:27]([CH2:26][CH2:25][C@:23]12[CH3:24])[C@:28]1([CH3:31])[C@@H:15]([CH2:14][C@@H:13]([OH:12])[CH2:30][CH2:29]1)[CH2:16][CH2:17]3

Participants

5

Reactant 2

HCID 109033043beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehydeHCID 178483810HCID 178483810, compound

Product 1

HCID 178483809HCID 178483809, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.64 g of 1-amino-3-(2-dimethylaminoethyl)guanidine hydroiodide (prepared following the procedure described in Houben-Weil, Metoden der Organischen Chemie, Band VIII, page 183) in 20 ml of 10-4M hydrochloric acid a solution of 1.10 g of 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde (Boutagy J. and Thomas R., Aust. J. Chem., 1971, 24, 2723) in 25 ml of dioxane was added dropwise at room temperature. After 3 hrs, the solution was evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 78/20/2 as eluant; the fractions containing the title compound were collected and evaporated to dryness. The residue was ground with di-iso-propyl ether to give 0.15 g of the title compound (I-ag) as hydroiodide, white solid.

Workup

  1. additionwas added dropwise at room temperature
  2. customthe solution was evaporated to dryness under reduced pressure
  3. customThe crude product was purified by flash-chromatography (SiO2)
  4. additionthe fractions containing the title compound
  5. customwere collected
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6f0f5a360baf4488ba679f750fbb5a35
Source dataset
uspto-grants-1996_07
Patent number
US05538960

Reaction notes

Loading…