Hydrochloric Acid → HCID 176525582, compound

HRID 1735740Notes

Reaction equation

HRID 1735740 reaction equation
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@:8]3([OH:24])[CH2:9][CH2:10][C@@H:11]2[C:12](=O)[CH3:13])[CH2:3]1.C(=O)(O)O.[NH2:29][NH:30][C:31]([NH2:33])=[NH:32].Cl>O1CCOCC1.O>[NH:30](/[N:29]=[C:12](/[C@@H:11]1[C@:15]2([CH3:23])[C@@:8]([OH:24])([C@H:7]3[C@H:18]([CH2:17][CH2:16]2)[C@:19]2([CH3:22])[C@@H:4]([CH2:3][C@@H:2]([OH:1])[CH2:21][CH2:20]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)\[CH3:13])[C:31]([NH2:33])=[NH:32]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12310535HCID 12310535, compoundHCID 178513185HCID 178513185, compound

Product 1

HCID 176525582HCID 176525582, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.00 g of 3β,14β-dihydroxy-5β-pregnane-20-one (Templeton J. F. et al., J. Chem. Soc., Perkin Trans. 1, 1991, 823), 1.20 g of aminoguanidine hydrogencarbonate in 40 ml of dioxane and 10 ml of water acidified at pH 2.5 with 0.01M hydrochloric acid was stirred at room temperature for 3 days. The precipitate was collected by filtration and purified by flash-chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 78/20/2; the fractions containing the title compound were collected and evaporated to dryness. The crude product was ground with ethanol to give 0.40 g of the title compound (I-bk) as a white solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. custompurified by flash-chromatography (SiO2)
  3. additionthe fractions containing the title compound
  4. customwere collected
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e701279276ac4f42a8027902a5aa64d8
Source dataset
uspto-grants-1996_07
Patent number
US05538960

Reaction notes

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