Sodium hydride → HCID 10289584, compound

HRID 1985133Notes

Reaction equation

HRID 1985133 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C([O:12][C:13](=[O:41])[C:14]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[F:40])([CH3:32])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:25]2[CH2:29][NH:28][C:27](=[O:30])[N:26]2[CH3:31])=[CH:18][CH:17]=1)C.[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:28]2[CH2:29][CH:25]([CH2:24][CH2:23][O:22][C:19]3[CH:18]=[CH:17][C:16]([CH2:15][C:14]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[F:40])([CH3:32])[C:13]([OH:41])=[O:12])=[CH:21][CH:20]=3)[N:26]([CH3:31])[C:27]2=[O:30])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 68867329HCID 68867329, compound

Product 1

HCID 10289584HCID 10289584, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Chlorobenzyl bromide (0.037 g, 0.179 mmol) 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. The organic layer is dried, concentrated, and purified by LCMS to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.31-7.21 (m, 4H), 7.16 (d, 2H, J=8.3 Hz), 7.11-7.00 (m, 4H), 6.74 (d, 2H, J=8.3 Hz), 4.33, 4.31 (ABq, 2H, J=15.5 Hz), 3.96 (t, 2H, J=6.0 Hz), 3.71-3.64 (m, 1H), 3.39 (t, 1H, J=8.3 Hz), 3.29, 3.17 (ABq, 2H, J=14.3 Hz), 3.01 (t, 1H, J=8.3 Hz), 2.84 (s, 3H), 2.25-2.20 (m, 1H), 1.93-1.84 (m, 1H), 1.41 (s, 3H). MS [ES+] m/z exact mass calcd for C29H31N2O5 541.1906, found 541.1913.

Workup

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

Sources & evidence

ORD record
ord-595ad253eeaa4ce5a737df2ba632e5d8
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

Loading…