Sodium Hydroxide → HCID 68869658, compound

HRID 1985186Notes

Reaction equation

HRID 1985186 reaction equation
C([O:3][C:4](=[O:42])[C:5]([CH3:41])([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH3:41][C:5]([O:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=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:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:11][CH:12]=1)[C:4]([OH:42])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68867449HCID 68867449, compound

Product 1

HCID 68869658HCID 68869658, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-methyl-3-{4-[2-(3-methyl-1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl ester (0.161 g, 0.284 mmol) in ethanol (8 mL) is treated with aqueous 5 N NaOH (0.75 mL) and heated to reflux 1 h. The reaction mixture is cooled, the solvent removed in vacuo. The resultant residue is acidified with aqueous 1 N HCl (10 mL) and extracted with CH2Cl2. The organic layer is dried (Na2SO4) and the solvent removed in vacuo to afford 0.113 g (74%) 2-methyl-3-{4-[2-(3-methyl-1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid. 1H NMR. HRMS (ES+) m/z exact mass calc'd for C33H35N2O5 (M+1) 539.2546. Found m/z 539.2548.

Workup

  1. temperatureheated
  2. temperatureto reflux 1 h
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent removed in vacuo
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-08a64564ece74f5ab0279a5a38701885
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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