HCID 20532007, compound → HCID 20532008, compound

HRID 1759368Notes

Reaction equation

HRID 1759368 reaction equation
[CH2:1]([C:4]1([C:13]([C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[O:17])([CH3:15])[CH3:14])[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]1=[O:12])[CH:2]=[CH2:3].[H][H]>[Pd].C(O)C>[CH2:1]([C:4]1([C:13]([C:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)=[O:17])([CH3:15])[CH3:14])[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]1=[O:12])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 20532007HCID 20532007, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20532008HCID 20532008, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 750 g. of 5-allyl-5-(p-aminophenyloxycarbonyl-isopropyl)barbituric acid in 15 ml. of ethanol containing 100 mg. of 10% palladium-on-carbon as catalyst was subjected to hydrogenation at room temperature and atmospheric pressure. After one hour, the required amount (180 ml.) of hydrogen had been taken up. The reaction mixture was filtered through Celite, and the filtrate was evaporated to dryness. The residue was chromatographed on 13 g. of silica gel with ethyl acetate as the eluent. Fractions containing the desired product were evaporated. The remaining solid was recrystallized from chloroform/ether to afford 620 mg. (89%) of the ester, m.p. 212°-215°.

Workup

  1. customwas subjected to hydrogenation at room temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was chromatographed on 13 g
  5. additionFractions containing the desired product
  6. customwere evaporated
  7. customThe remaining solid was recrystallized from chloroform/ether
  8. customto afford 620 mg

Sources & evidence

ORD record
ord-9eba8a93e59d45a581b72462ba8191fb
Source dataset
uspto-grants-1982_07
Patent number
US04340736

Reaction notes

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