1,4-Dioxane hydrochloride → HCID 57320402, compound

HRID 1900761Notes

Reaction equation

HRID 1900761 reaction equation
C([NH:11][C@H:12]([C:14]([NH:16][CH2:17][CH:18]1[O:32][C:21]2=[C:22]3[C:27](=[C:28]([CH3:30])[CH:29]=[C:20]2[CH2:19]1)[NH:26][C:25](=[O:31])[CH:24]=[CH:23]3)=[O:15])[CH3:13])(OCC1C=CC=CC=1)=O.[H][H].O1CCOCC1.Cl>CN(C)C=O.CO.[Pd]>[NH2:11][C@H:12]([C:14]([NH:16][CH2:17][CH:18]1[O:32][C:21]2=[C:22]3[C:27](=[C:28]([CH3:30])[CH:29]=[C:20]2[CH2:19]1)[NH:26][C:25](=[O:31])[CH:24]=[CH:23]3)=[O:15])[CH3:13]

Participants

7

Reactant 3

HCID 204431481,4-Dioxane hydrochlorideHCID 22867054HCID 22867054, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57320402HCID 57320402, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The compound obtained in Example 224 (3.0 g, 6.9 mmol) was dissolved in dimethylformamide (200 ml). To the obtained solution, 10% palladium-on-carbon (3.0 g) was added, followed by stirring at room temperature overnight in the atmosphere of hydrogen. The reaction mixture was filtered, and the filtrate was condensed under reduced pressure. The resultant residue was dissolved in methanol (20 ml), and 4N-HCl dioxane (4 ml) was added thereto while cooling on ice. The mixture was condensed under reduced pressure. The resultant residue was recrystallized from methanol--ether to obtain 1.5 g of the title compound as pale yellow powdery crystals (64.4%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed under reduced pressure
  3. temperaturewhile cooling on ice
  4. customcondensed under reduced pressure
  5. customThe resultant residue was recrystallized from methanol

Sources & evidence

ORD record
ord-0f712caf49104953b3783b5e9f9db7db
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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