Water → Benzyl ((S)-4-(4-formylphenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetate

HRID 1883091Notes

Reaction equation

HRID 1883091 reaction equation
[PH2]([O-])=O.[Na+].[OH2:5].[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C@@:14]2([CH3:39])[C:18](=[O:19])[N:17]([CH2:20][C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[C:16](=[O:31])[N:15]2[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:10][CH:9]=1)#N>[Ni].N1C=CC=CC=1.C(O)(=O)C.O>[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([C@@:14]2([CH3:39])[C:18](=[O:19])[N:17]([CH2:20][C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[C:16](=[O:31])[N:15]2[CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:10][CH:9]=1)=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 86588625Benzyl ((S)-4-(4-cyanophenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetateHCID 178527019HCID 178527019, compound

Product 1

HCID 86588626Benzyl ((S)-4-(4-formylphenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetateYield 79%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 67720230HCID 67720230, compoundSolvent

Conditions

Temperature
60 °C

Procedure

24.3 g of sodium hypophosphite×H2O and 4.02 g of Raney nickel were added to a solution of 6.08 g (13.42 mmol) of 8.1 in 200 ml of pyridine/acetic acid/water (2:1:1) at 0° C. and the reaction mixture was heated at 60° C. for 8 h. After cooling to room temperature and filtration, the reaction mixture was concentrated in vacuo, the residue was taken up in ethyl acetate and the ethyl acetate phase was extracted 2× with water, 2× with 10% strength citric acid solution, 2× with saturated NaHCO3 solution and with saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and, after filtration, the solvent was removed in vacuo. 4.82 g (79%) of 8.2 were obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltration
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. extractionthe ethyl acetate phase was extracted 2× with water, 2× with 10% strength citric acid solution, 2× with saturated NaHCO3 solution
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationafter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5a2023e123f14d848e41d031461837f3
Source dataset
uspto-grants-2004_07
Patent number
US06759424B2

Reaction notes

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