HCID 19088032, compound → HCID 14031665, compound

HRID 1464514Notes

Reaction equation

HRID 1464514 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-b8b6728ed66a450cb20ec55975b4d3a6
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

Loading…