Sodium Hydroxide → [1-(4-Methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid

HRID 1985178Notes

Reaction equation

HRID 1985178 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:7](=[O:19])[N:6]1[CH2:20][CH2:21][CH3:22].[OH-].[Na+]>CO>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:8]2[C:9](=[O:10])[CH:5]([CH2:4][C:3]([OH:23])=[O:2])[N:6]([CH2:20][CH2:21][CH3:22])[C:7]2=[O:19])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57719188HCID 57719188, compound

Product 1

HCID 57719268[1-(4-Methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [1-(4-methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid methyl ester (1.67 g, 5.20 mmol) in methanol (40 mL) is treated with aqueous 5 N NaOH (4.4 mL) and heated to reflux 1.5 hour. The reaction mixture is cooled, the solvent removed. The resultant residue is acidified and extracted with EtOAc. The organic layer is dried and dried to afford 1.56 g (98%) [1-(4-methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid. 1H NMR. MS (ES−) Calc'd for C16H19N2O4 (M−1) 303. Found m/z 303 (100%).

Workup

  1. temperatureheated
  2. temperatureto reflux 1.5 hour
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent removed
  5. extractionextracted with EtOAc
  6. customThe organic layer is dried
  7. customdried

Sources & evidence

ORD record
ord-04a48bad54b34e53aa91b2a30d28221b
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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