Sodium Hydroxide → HCID 68867550, compound

HRID 1985181Notes

Reaction equation

HRID 1985181 reaction equation
C([O:3][C:4](=[O:41])[C:5]([CH3:40])([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[C:18](=[O:29])[N:17]2[CH2:30][CH2:31][CH3:32])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH3:40][C:5]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:18](=[O:29])[N:17]2[CH2:30][CH2:31][CH3:32])=[CH:11][CH:12]=1)[C:4]([OH:41])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68867360HCID 68867360, compound

Product 1

HCID 68867550HCID 68867550, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester (0.456 g, 0.816 mmol) in ethanol (20 mL) is treated with aqueous 5 N NaOH (2 mL) and heated to reflux 1 h. The reaction mixture is cooled, the solvent removed. The resultant residue is acidified and extracted with CH2Cl2. The organic layer is dried and the solvent removed to afford 0.419 g (97%) 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid. 1H NMR. HRMS (ES+) m/z exact mass calc'd for C32H39N2O5 (M+1) 531.2859. Found m/z 531.2866.

Workup

  1. temperatureheated
  2. temperatureto reflux 1 h
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent removed
  5. extractionextracted with CH2Cl2
  6. customThe organic layer is dried
  7. customthe solvent removed

Sources & evidence

ORD record
ord-bea1a052b43b40c2926ca4c0190499aa
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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