Sodium hydride → 2-(2-Fluoro-phenoxy)-3-(4-{2-[1-(3-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester

HRID 1985146Notes

Reaction equation

HRID 1985146 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[CH2:11]([O:13][C:14](=[O:42])[C:15]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[F:41])([CH3:33])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH:26]2[CH2:30][NH:29][C:28](=[O:31])[N:27]2[CH3:32])=[CH:19][CH:18]=1)[CH3:12].[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:11]([O:13][C:14](=[O:42])[C:15]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[F:41])([CH3:33])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH:26]2[CH2:30][N:29]([CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:28](=[O:31])[N:27]2[CH3:32])=[CH:19][CH:18]=1)[CH3:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 40672073-Methoxybenzyl bromideHCID 68867329HCID 68867329, compound

Product 1

HCID 101751012-(2-Fluoro-phenoxy)-3-(4-{2-[1-(3-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Methoxybenzyl bromide (0.03 mL, 0.179 mmol, d=1.436) and tetrabutyl ammonium iodide (catalytic amount) are added to a 0° C. suspension of 2-(2-Fluoro-phenoxy)-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester (0.053 g, 0.119 mmol) and sodium hydride (0.012 g, 0.298 mmol, 60% suspension on mineral oil), and pre-stirred for 1 h at ambient temperature. The reaction mixture is stirred at ambient temperature for 18 h, diluted with ethyl acetate, and washed. The organic layer is dried, concentrated, and carried into the next step. MS [EI+] 565 (M+H)+.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 18 h
  2. washwashed
  3. customThe organic layer is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2b0a4c6cecb04db59127fbe79d105801
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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