HCID 176518681, compound → HCID 178421252, compound

HRID 1449481Notes

Reaction equation

HRID 1449481 reaction equation
Cl.[NH:2](/[N:6]=[CH:7]/[C@H:8]1[CH2:13][CH2:12][C@:11]2([OH:28])[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C@@H:17]([CH2:18][C@@H:19]([OH:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)[C:3]([NH2:5])=[NH:4]>C(O)C.[Pt](=O)=O>[C:3]([NH:2][NH:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@:11]2([OH:28])[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C@@H:17]([CH2:18][C@@H:19]([OH:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)(=[NH:4])[NH2:5]

Participants

4

Reactant 1

HCID 176518681HCID 176518681, compound

Product 1

HCID 178421252HCID 178421252, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.50 g of (E)-17β-guanidinoiminomethyl-5β-androstane-3β,14β-diol hydrochloride (prepared following the procedure described in DE 4,227,626 for similar compounds) and 0.40 g of platinum dioxide in 25 ml of ethanol was hydrogenated at 4.2 atm and room temperature for 8 hrs under shaking. The mixture was filtered and the solution evaporated under reduced pressure. The residue was cristallized from ethanol/ethyl acetate to give 0.30 g of the title compound (I-aa) as a white solid, hydrochloride.

Workup

  1. customprepared
  2. filtrationThe mixture was filtered
  3. customthe solution evaporated under reduced pressure

Sources & evidence

ORD record
ord-cb5abe793dc04003a786fd94e3b431b9
Source dataset
uspto-grants-1997_02
Patent number
US05599806

Reaction notes

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