Hydrogen Bromide → HCID 88140984, compound

HRID 725260Notes

Reaction equation

HRID 725260 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[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:34])[C@:17]3([OH:35])[CH2:18][CH2:19][C@@H:20]2/[CH:21]=[C:22](\[CH3:25])/[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]/[C:22](/[CH3:25])=[CH:21]/[C@H:20]1[CH2:19][CH2:18][C@:17]2([OH:35])[C@H:16]3[C@H:29]([CH2:28][CH2:27][C@:26]12[CH3:34])[C@:30]1([CH3:33])[C@@H:13]([CH2:12][C@@H:11]([OH:10])[CH2:32][CH2:31]1)[CH2:14][CH2:15]3

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 30850992-Hydrazino-delta-2-imidazoline hydrobromideHCID 10666253(E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxaldehyde

Product 1

HCID 88140984HCID 88140984, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 0.55 g of 2-hydrazino-2-imidazoline hydrobromide in 10 ml of water and 30 ml of dioxane was made acid to pH 3 with 0.1N HBr. A solution of 1.00 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 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 0.85 g of the title compound (I-ab) 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-dee9a60778074b558b605bba2e506c4e
Source dataset
uspto-grants-1998_01
Patent number
US05705662

Reaction notes

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