HCID 67800901, compound → HCID 67801453, compound

HRID 1900763Notes

Reaction equation

HRID 1900763 reaction equation
[NH2:1][C@@H:2]([C:4]([NH:6][CH2:7][CH:8]1[O:22][C:11]2=[C:12]3[C:17](=[C:18]([CH3:20])[CH:19]=[C:10]2[CH2:9]1)[NH:16][C:15](=[O:21])[CH:14]=[CH:13]3)=[O:5])[CH3:3].[H][H]>O.[Pd]>[NH2:1][C@@H:2]([C:4]([NH:6][CH2:7][CH:8]1[O:22][C:11]2=[C:12]3[C:17](=[C:18]([CH3:20])[CH:19]=[C:10]2[CH2:9]1)[NH:16][C:15](=[O:21])[CH2:14][CH2:13]3)=[O:5])[CH3:3]

Participants

5

Reactant 2

HCID 67800901HCID 67800901, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67801453HCID 67801453, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

The compound obtained in Example 228 (680 mg, 2.0 mmol) was dissolved in water (30 ml). To the obtained solution, 10% palladium-on-carbon (600 mg) was added, followed by stirring at 80° C. for 10 hours in the atmosphere of hydrogen. The reaction mixture was filtered, and the filtrate was condensed under reduced pressure. The resultant residue was purified by silica gel column chromatography (chloroform: methanol =5:1). The obtained crystals were dissolved in methanol (5 ml), and 4N-HCl dioxane (1 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 300 mg of the title compound as colorless powdery crystals (44.1%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed under reduced pressure
  3. customThe resultant residue was purified by silica gel column chromatography (chloroform: methanol =5:1)
  4. dissolutionThe obtained crystals were dissolved in methanol (5 ml)
  5. addition4N-HCl dioxane (1 ml) was added
  6. temperaturewhile cooling on ice
  7. customcondensed under reduced pressure
  8. customThe resultant residue was recrystallized from methanol

Sources & evidence

ORD record
ord-c8ebc09f51524d39a7af6da5c4357beb
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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