Benzyl Bromide → HCID 68867323, compound

HRID 1985131Notes

Reaction equation

HRID 1985131 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:40])[C:13]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[F:39])([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:40])[C:13]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[F:39])([CH3:31])[CH2:14][C:15]1[CH:20]=[CH:19][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:17][CH:16]=1)[CH3:10]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 68867329HCID 68867329, compound

Product 1

HCID 68867323HCID 68867323, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromide (0.02 mL, 0.172 mmol, d=1.438) 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 (0.051 g, 0.115 mmol) and sodium hydride (0.011 g, 0.287 mmol, 60% suspension on mineral oil), 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 with 1N HCl, water, and brine. The organic layer is dried and concentrated in vacuo to provide the title compound, which is used in the next step. MS [EI+] 535 (M+H)+.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 18 h
  2. washwashed with 1N HCl, water, and brine
  3. customThe organic layer is dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ab18437883a4980a0f0846827e008db
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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