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Benzyl Bromide → HCID 68867323, compound

HRID 1985140
Notes
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Reaction equation

HRID 1985140 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8857
Ethyl Acetate
Solvent

Procedure

Benzyl bromide (0.02 mL, 0.179 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 (0.053 g, 0.119 mmol) and sodium hydride (0.012 g, 0.298 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 over MgSO4 and concentrated in vacuo to provide the title compound, which is carried into 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. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b03bcbc6012547a7926b4fb38ef7fb25
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07544812B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes