Ethyl 2-(3-(4-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate → HCID 68541940, compound

HRID 1994304Notes

Reaction equation

HRID 1994304 reaction equation
C([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][N:16]([CH:19]([CH:25]([CH3:27])[CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]2=[O:28])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][N:16]([CH:19]([CH:25]([CH3:27])[CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]2=[O:28])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 68538627Ethyl 2-(3-(4-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrateHCID 178418361HCID 178418361, compound

Product 1

HCID 68541940HCID 68541940, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-(3-(4-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (400 mg; 0.97 mmol) was dissolved in ethanol (20 ml). Pd(OH)2 (100 mg; 0.71 mmol) was added thereto, and hydrogenation was carried out under about 1 atm. of hydrogen for 3 h. The catalyst was filtered off through kieselguhr and washed with ethanol (2×; 20 ml). The solvent was removed under reduced pressure. Purification of the residue by column chromatography (SiO2) resulted in ethyl 2-(3-(4-hydroxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (300 mg; 0.94 mmol). MS: 321.35 (M+H); Rt: 1.24 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. filtrationThe catalyst was filtered off through kieselguhr
  2. washwashed with ethanol (2×; 20 ml)
  3. customThe solvent was removed under reduced pressure
  4. customPurification of the residue by column chromatography (SiO2)

Sources & evidence

ORD record
ord-5d7a6f14a59f4bedad1b9e3827ae5b7a
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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