Cesium carbonate → 2-(4-{2-[1-(4-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1985117Notes

Reaction equation

HRID 1985117 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[CH2:12][CH:11]([CH2:13][CH2:14][O:15]S(C3C=CC(C)=CC=3)(=O)=O)[N:10]([CH3:26])[C:9]2=[O:27])=[CH:5][CH:4]=1.[CH2:30]([O:32][C:33](=[O:46])[C:34]([O:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][C:39]=1[CH3:45])([CH3:36])[CH3:35])[CH3:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:30]([O:32][C:33](=[O:46])[C:34]([O:37][C:38]1[CH:43]=[CH:42][C:41]([O:15][CH2:14][CH2:13][CH:11]2[CH2:12][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:29][CH:28]=3)[C:9](=[O:27])[N:10]2[CH3:26])=[CH:40][C:39]=1[CH3:45])([CH3:35])[CH3:36])[CH3:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 57719164Toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl ester

Product 1

HCID 101956842-(4-{2-[1-(4-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-2-methyl-phenoxy)-2-methyl-propionic acid ethyl esterYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl ester (0.100 g, 0.239 mmole) and 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (0.063 g, 0.262 mmole) in anhydrous DMF (2.0 mL), is added cesium carbonate (0.093 g, 0.287 mmole). After heating at 65° C. for about 16 hours, the reaction mixture is partitioned between ethyl acetate (5 ml) and 1.0 N HCl aq. (5 ml), the aqueous layer is extracted with more ethyl acetate (2×5 ml). The combined organic layer is washed with brine (3×5 ml). The organic layer is dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography using silica gel (0-40% acetone/hexane) produces a colorless oil (0.107 g, 91%). Mass [EI+] 485 (M+H)+.

Workup

  1. customthe reaction mixture is partitioned between ethyl acetate (5 ml) and 1.0 N HCl aq. (5 ml)
  2. extractionthe aqueous layer is extracted with more ethyl acetate (2×5 ml)
  3. washThe combined organic layer is washed with brine (3×5 ml)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-777d87f7de6445f89a9c0d58034e2b8a
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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