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

HRID 1985154Notes

Reaction equation

HRID 1985154 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:39])[C:15]([O:34][CH2:35][CH2:36][CH2:37][CH3:38])([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:39])[C:15]([O:34][CH2:35][CH2:36][CH2:37][CH3:38])([CH3:33])[CH2:16][C:17]1[CH:18]=[CH:19][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:21][CH:22]=1)[CH3:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 40672073-Methoxybenzyl bromideHCID 688675082-Butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester

Product 1

HCID 688700622-Butoxy-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 (0.024 mL, 0.170 mmol, d=1.436) and tetrabutyl ammonium iodide (catalytic amount) are added to a 0° C. suspension of 2-butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester (0.046 g, 0.114 mmol) and sodium hydride (0.011 g, 0.28 mmol, 60% suspension on mineral oil), pre-stirred for 1 h at ambient temperature. The reaction mixture is stirred at ambient temperature 48 h, diluted with ethyl acetate, and washed with 1N HCl and water. The organic layer is dried, concentrated, and used in the next step. MS [EI+] 527 (M+H)+.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature 48 h
  2. washwashed with 1N HCl and water
  3. customThe organic layer is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-df5fea484bf74b7da62cb1e7904ae09f
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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