Nitrogen → 2-(4-{2-[1-(3,4-Dimethyl-benzyl)-3-(4-methoxy-benzyl)-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1985235

Reaction equation

HRID 1985235 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[CH3:37])[CH2:5][N:6]1[CH2:10][CH:9]([CH2:11][CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)[N:8]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:7]1=[O:33].[CH2:38]([O:40][C:41](=[O:53])[C:42]([O:45][C:46]1[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=1)([CH3:44])[CH3:43])[CH3:39].N#N>CN(C=O)C>[CH2:38]([O:40][C:41](=[O:53])[C:42]([O:45][C:46]1[CH:47]=[CH:48][C:49]([O:52][CH2:12][CH2:11][CH:9]2[CH2:10][N:6]([CH2:5][C:4]3[CH:34]=[CH:35][C:36]([CH3:37])=[C:2]([CH3:1])[CH:3]=3)[C:7](=[O:33])[N:8]2[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[CH:50][CH:51]=1)([CH3:44])[CH3:43])[CH3:39]

Participants

5

Reactant 3

HCID 947NitrogenHCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoateHCID 57719167Toluene-4-sulfonic acid 2-[1-(3,4-dimethyl-benzyl)-3-(4-methoxy-benzyl)-2-oxo-imidazolidin-4-yl]-ethyl ester

Product 1

HCID 577189882-(4-{2-[1-(3,4-Dimethyl-benzyl)-3-(4-methoxy-benzyl)-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl esterYield 108.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of toluene-4-sulfonic acid 2-[1-(3,4-dimethyl-benzyl)-3-(4-methoxy-benzyl)-2-oxo-imidazolidin-4-yl]-ethyl ester (2.54 g, 4.86 mmol), 2-(4-hydroxy-phenoxy)-2-methyl-propionic acid ethyl ester (0.99 g, 4.01 mmol) and CS2CO3 (1.73 g, 5.31 mmol) in DMF (60 mL) was heated at 55° C. for under N2 for 16 h. The reaction mixture was cooled to room temperature, quenched with aqueous 1 N HCl (25 mL), and worked up extractively with EtOAc and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 4:1 hexanes:acetone to afford 2.51 g (99%) 2-(4-{2-[1-(3,4-dimethyl-benzyl)-3-(4-methoxy-benzyl)-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester. MS (ES+) Calc'd for C34H43N2O6 (M+1) 575. Found m/z 575 (100%). 1H NMR.

Workup

  1. customquenched with aqueous 1 N HCl (25 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto afford crude product that
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e5036b9191fc4336b4afbdbaa91ad6b3
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Linked notes

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