Hydrogen Bromide → (3S,5R,8R,9S,10S,13R,14S,17R)-17-[(E,3E)-3-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)prop-1-enyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,14-diol

HRID 1080629Notes

Reaction equation

HRID 1080629 reaction equation
Br.[NH:2]([C:4]1[NH:5][CH2:6][CH2:7][N:8]=1)[NH2:3].Br.[OH:10][C@H:11]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:33])[C@:17]3([OH:34])[CH2:18][CH2:19][C@@H:20]2/[CH:21]=[CH:22]/[CH:23]=O)[CH2:12]1>O.O1CCOCC1>[NH:8]1[CH2:7][CH2:6][N:5]=[C:4]1[NH:2]/[N:3]=[CH:23]/[CH:22]=[CH:21]/[C@H:20]1[CH2:19][CH2:18][C@:17]2([OH:34])[C@H:16]3[C@H:28]([CH2:27][CH2:26][C@:25]12[CH3:33])[C@:29]1([CH3:32])[C@@H:13]([CH2:12][C@@H:11]([OH:10])[CH2:31][CH2:30]1)[CH2:14][CH2:15]3

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 30850992-Hydrazino-delta-2-imidazoline hydrobromideHCID 10736377(E)-3beta,14beta-dihydroxy-5beta-pregn-20-ene-21-carboxaldehyde

Product 1

HCID 15292612(3S,5R,8R,9S,10S,13R,14S,17R)-17-[(E,3E)-3-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)prop-1-enyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,14-diolYield 59.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1.19 g of 2-hydrazino-2-imidazoline hydrobromide in 20 ml of water and 60 ml of dioxane was made acid to pH 3 with 0.1N HBr. A solution of 2.08 g of (E)-3β,14β-dihydroxy-5β-pregn-20-ene-21-carboxaldehyde (Fullerton D. S. et al., J. Med. Chem., 1976, 19, 1330) in 25 ml of dioxane was added at room temperature. After 3 days, the solution was evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 90/10/1 as the eluant; the fractions containing the title compound were collected and evaporated to dryness. The residue was ground with ethyl acetate and ethanol to give 1.54 g of the title compound (I-ac) as a white solid.

Workup

  1. customthe solution 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

Sources & evidence

ORD record
ord-1ccbac334e3948bbb594d4eb0e0b0e82
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

Loading…