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

HRID 1985263Notes

Reaction equation

HRID 1985263 reaction equation
C([O:3][C:4](=[O:35])[CH:5]([O:31][CH:32]([CH3:34])[CH3:33])[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]([OH:28])=[CH:24][CH:23]=3)[C:18](=[O:29])[N:17]2[CH3:30])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[OH:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:19]2[CH2:20][CH:16]([CH2:15][CH2:14][O:13][C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([O:31][CH:32]([CH3:33])[CH3:34])[C:4]([OH:35])=[O:3])=[CH:8][CH:9]=3)[N:17]([CH3:30])[C:18]2=[O:29])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 688699793-(4-{2-[1-(4-Hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester

Product 1

HCID 688671073-(4-{2-[1-(4-Hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(4-{2-[1-(4-hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester (0.048 g, 0.089 mmol) in ethanol (8 mL) was treated with aqueous 5 N NaOH (1.5 mL) and stirred at room temperature for 2 h. The solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (15 mL) and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 0.038 g (84%) 3-(4-{2-[1-(4-hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy- propionic acid. 1H NMR (500 MHz, CDCl3) δ 7.49 (d, 2H, J=8.07 Hz), 7.30 (d, 2H, J=8.07 Hz), 7.06 (d, 2H, J=8.31 Hz), 6.66 (d, 2H, J=8.31 Hz), 4.40, 4.31 (ABq, 2H, J=15.65 Hz), 4.03-4.01 (m, 1H), 3.90 (t, 2H, J=5.87 Hz), 3.59-3.53 (m, 1H), 3.48 (hp, 1H, J=5.87 Hz), 3.31 (t, 1H, J=8.80 Hz), 3.12-2.96 (m, 1H), 2.95 (t, 1H, J=8.80 Hz), 2.90-2.79 (m, 1H), 2.78 (s, 3H), 2.27-2.23 (m, 1H), 1.93-1.84 (m, 1H), 1.14 (d, 3H, J=5.87 Hz), 0.97 (d, 3H, J=5.87 Hz). HRMS (ES+) m/z exact mass calc'd for C26H32N2O5F3 (M+1) 509.2274. Found m/z 509.2263.

Workup

  1. customThe solvent removed in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-657b890dfda746519e74ea419fdb6a3b
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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