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]prop-2-enylidene]amino]guanidine

HRID 1080628Notes

Reaction equation

HRID 1080628 reaction equation
C(=O)(O)O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].Cl.[OH:11][C@H:12]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:34])[C@:18]3([OH:35])[CH2:19][CH2:20][C@@H:21]2/[CH:22]=[CH:23]/[CH:24]=O)[CH2:13]1>O.O1CCOCC1>[NH:6](/[N:5]=[CH:24]/[CH:23]=[CH:22]/[C@H:21]1[CH2:20][CH2:19][C@:18]2([OH:35])[C@H:17]3[C@H:29]([CH2:28][CH2:27][C@:26]12[CH3:34])[C@:30]1([CH3:33])[C@@H:14]([CH2:13][C@@H:12]([OH:11])[CH2:32][CH2:31]1)[CH2:15][CH2:16]3)[C:7]([NH2:9])=[NH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10736377(E)-3beta,14beta-dihydroxy-5beta-pregn-20-ene-21-carboxaldehydeHCID 178513185HCID 178513185, compound

Product 1

HCID 1765255681-[(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]prop-2-enylidene]amino]guanidineYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 1.05 g of aminoguanidine hydrogencarbonate in 23 ml of water and 70 ml of dioxane was made acid to pH 3 with 3N HCl. 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 20 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 1.58 g of the title compound (I-aa) as a white solid.

Workup

  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

Sources & evidence

ORD record
ord-ac32a25b35154743b99dbaefbf723756
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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