Benzyl Bromide → 3-{4-[2-(1-Benzyl-3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-butoxy-2-methyl-propionic acid ethyl ester

HRID 1985152Notes

Reaction equation

HRID 1985152 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:37])[C:13]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])([CH3:31])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH:24]2[CH2:28][NH:27][C:26](=[O:29])[N:25]2[CH3:30])=[CH:17][CH:16]=1)[CH3:10].[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:9]([O:11][C:12](=[O:37])[C:13]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])([CH3:31])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][CH:24]2[CH2:28][N:27]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:26](=[O:29])[N:25]2[CH3:30])=[CH:19][CH:20]=1)[CH3:10]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 688675082-Butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester

Product 1

HCID 688667853-{4-[2-(1-Benzyl-3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-butoxy-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromide (0.0.21 mL, 0.174 mmol, d=1.438) 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 (0.047 g, 0.116 mmol) and sodium hydride (0.012 g, 0.29 mmol, 60% suspension on mineral oil), pre-stirred for 1 h at ambient temperature. The reaction mixture is stirred at ambient temperature for 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+] 497 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-7dd368b5752a47e38722e43af18761e2
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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