HCID 19088032, compound → HCID 14031665, compound

HRID 1646810Notes

Reaction equation

HRID 1646810 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][CH2:21][C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:19]>C(O)C.[Pd]>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19]

Participants

4

Reactant 1

HCID 19088032HCID 19088032, compound

Product 1

HCID 14031665HCID 14031665, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoylglycinate (0.78 g) in ethanol (8 ml) was hydrogenated in the presence of 5% palladium-charcoal (0.08 g) at room temperature. After the reaction was completed, the catalyst was removed by filtration. The solution was treated with ferric chloride (0.51 g) in water (5 ml) at room temperature for 20 min. with stirring. The reaction mixture was worked up in the usual manner. The product was recrystallized from ethylacetate to give 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoylglycine (0.63 g, 98%), mp 162°-164° C.

Workup

  1. customthe catalyst was removed by filtration
  2. additionThe solution was treated with ferric chloride (0.51 g) in water (5 ml) at room temperature for 20 min.
  3. customThe product was recrystallized from ethylacetate

Sources & evidence

ORD record
ord-e84773d755c244f29661cafbdf442def
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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