HCID 19779195, compound → HCID 135588784, compound

HRID 2081959Notes

Reaction equation

HRID 2081959 reaction equation
[CH3:1][C:2]([C:5]1[C:6](=[O:23])[C:7]([C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[CH:8][C:9](=[N:11][C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[CH:10]=1)([CH3:4])[CH3:3]>C(OCC)(=O)C.[C].[Pd]>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([NH:11][C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[C:7]([C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])[C:6]=1[OH:23])([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 19779195HCID 19779195, compound

Product 1

HCID 135588784HCID 135588784, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In 450 ml of ethyl acetate was dissolved 2.5 g of Compound 1a followed by addition of 0.30 g of 10% palladium-carbon as a catalyst. After purging the atmosphere in the reaction vessel with hydrogen gas, the reaction mixture was stirred at ambient temperature. After 180 ml of hydrogen had been consumed, the reaction mixture was filtered through Celite to remove the catalyst and the filtrate was washed with ethyl acetate and concentrated under reduced pressure. The crude product thus obtained was washed with diethyl ether to give 2.3 g of the desired compound as a colorless solid. The structure and physical properties of the product compound are shown in Table 2.

Workup

  1. customAfter purging the atmosphere in the reaction vessel with hydrogen gas
  2. customAfter 180 ml of hydrogen had been consumed
  3. filtrationthe reaction mixture was filtered through Celite
  4. customto remove the catalyst
  5. washthe filtrate was washed with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product thus obtained
  8. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-4b08805945ed4a47a51f463a302f8fb7
Source dataset
uspto-grants-1993_02
Patent number
US05187161

Reaction notes

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