Sodium Hydroxide → 3-(4-{2-[1-(3-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid

HRID 1985188Notes

Reaction equation

HRID 1985188 reaction equation
C([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[C:18](=[O:30])[N:17]2[CH3:31])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][N:19]1[CH2:20][CH:16]([CH2:15][CH2:14][O:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C:5]([CH3:39])([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:4]([OH:40])=[O:3])=[CH:12][CH:11]=2)[N:17]([CH3:31])[C:18]1=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 688696793-(4-{2-[1-(3-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester

Product 1

HCID 688668373-(4-{2-[1-(3-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(4-{2-[1-(3-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (0.28 g, 0.51 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 in vacuo. The resultant residue is acidified with aqueous 1 N HCl (20 mL) and extracted with CH2Cl2. The organic layer is dried (Na2SO4) and the solvent removed in vacuo to afford 0.257 g (97%) 3-(4-{2-[1-(3-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid 1H NMR (500 MHz, CDCl3) □ 7.28-7.20 (m, 3H), 7.18 (d, 2H, J=8.80 Hz), 7.04 (t, 1H, J=7.34 Hz), 6.91 (d, 2H, J=7.83 Hz), 6.82 (t, 1H, J 7.83 Hz), 6.79-6.78 (m, 2H), 6.73 (d, 2H, J=8.83 Hz), 4.38, 4.28 (ABq, 2H, J=14.92 Hz), 3.95 (t, 2H, J=5.87 Hz), 3.77 (s, 3H), 3.60 (ddd, 1H, J=12.2 Hz, J=8.40 Hz, J=3.42 Hz), 3.36 (t, 1H, J=7.83 Hz), 3.30, 3.10 (ABq, 2H, J=13.69 Hz), 2.96 (t, 1H, J=7.83 Hz), 2.83 (s, 3H), 2.25-2.18 (m, 1H), 1.92-1.84 (m, 1H), 1.42 (s, 3H). HRMS (ES+) m/z exact mass calc'd for C30H35N2O6 (M+1) 519.2495. Found m/z 519.2504.

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-42efc42b9c7e4f06a6cc18179ae32b3c
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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