Iodoethane → HCID 10289984, compound

HRID 1985168Notes

Reaction equation

HRID 1985168 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C:5]([CH3:40])([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[C:18](=[O:32])[NH:17]2)=[CH:9][CH:8]=1)[CH3:2].[H-].[Na+].I[CH2:45][CH3:46]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:41])[C:5]([CH3:40])([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2[CH2:45][CH3:46])=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 688700092-Methyl-3-(4-{2-[2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

Product 1

HCID 10289984HCID 10289984, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of 2-Methyl-3-(4-{2-[2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester (0.500 g, 0.875 mmol) and sodium hydride (0.039 g, 0.96 mmol, 60% dispersion on mineral oil) in DMF (10 mL) is stirred for 1 hour, then cooled to 0° C. Iodoethane (0.70 mL, 8.75 mmol, d=1.975) is added, then the reaction mixture is stirred 18 hours at ambient temperature and diluted with ethyl acetate. The organic layer is washed, dried, and concentrated to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.55 (d, 2 h, J=8.8 Hz), 7.37 (d, 2H, J=8.0 Hz), 7.21 (t, 2H, J=8.8 Hz), 7.15 (d, 2H, J=8.0 Hz), 6.96 (t, 1H, J=7.2 Hz), 6.82 (d, 2H, J=7.2 Hz), 6.74 (d, 2H, J=8.8 Hz), 4.43, 4.39 (ABq, 2H, J=15.2 Hz), 4.22, 4.17 (ABq, 2H, J=7.2 Hz), 3.96 (t, 1H, J=6.4 Hz), 3.85-3.78 (m, 1H), 3.61-3.55 (m, 1H), 3.35 (t, 1H, J=8.8 Hz), 3.26, 3.12 (ABq, 2H, J=13.6 Hz), 3.16-3.07 (m, 2H), 2.99 (t, 1H, J=8.0 Hz), 2.26-2.19 (m, 1H), 1.90-1.83 (m, 1H), 1.39(s, 3H), 1.21 (t, 3H, J=7.2 Hz), 1.14 (t, 3H, J=7.2 Hz). MS [EI+] 599 (M+H)+.

Workup

  1. washThe organic layer is washed
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3d00f4f0c4fb42f899df4bb95bbb1364
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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