Cesium carbonate → HCID 68866813, compound

HRID 1985159Notes

Reaction equation

HRID 1985159 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:9][C:10](=[O:40])[C:11]([OH:39])([CH3:38])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]2[CH2:26][N:25]([CH2:27][C:28]3[CH:33]=[CH:32][C:31](OC)=[CH:30][CH:29]=3)[C:24](=[O:36])[N:23]2[CH3:37])=[CH:15][CH:14]=1)[CH3:8].CN1C(CCOS(C2C=CC(C)=CC=2)(=O)=O)CN(CC2C=CC([C:67]([F:70])([F:69])[F:68])=CC=2)C1=O>CN(C=O)C.C(OCC)(=O)C>[CH2:7]([O:9][C:10](=[O:40])[C:11]([OH:39])([CH3:38])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH:22]2[CH2:26][N:25]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([C:67]([F:70])([F:69])[F:68])=[CH:32][CH:33]=3)[C:24](=[O:36])[N:23]2[CH3:37])=[CH:17][CH:18]=1)[CH3:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 68867294HCID 68867294, compoundHCID 86596229HCID 86596229, compound

Product 1

HCID 68866813HCID 68866813, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (8.72 g, 26.76 mmol) is added to a solution of 2-hydroxy-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester (2.0 g, 8.92 mmol) and Toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (4.34 g, 9.51 mmol) in DMF (50 mL). The resultant mixture is stirred at 55° C. under an atmosphere of nitrogen for 18 h, then diluted with ethyl acetate. The organic layer is washed, dried, concentrated, and purified by flash chromatography (25% acetone in hexanes) to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.95 (s, 1H), 7.50 (d, 2H, J=8.2 Hz), 7.32 (d, 2H, J=8.2 Hz), 7.03 (d, 2H, J=8.2 Hz), 6.65 (d, 2H, J=8.2 Hz), 4.40, 4.32 (ABq, 2H, J=14.7 Hz), 4.14-4.07 (m, 2H), 3.91 (t, 2H, J=5.7 Hz), 3.61-3.55 (m, 1H), 3.33 (t, 1H, J=8.2 Hz), 2.96-2.79 (m, 6H), 2.22-2.15 (m, 1H), 1.87-1.80 (m, 1H), 1.40 (s, 3H), 1.21 (t, 3H, J=7.4 Hz). Rf=0.38 in 50% acetone in hexanes.

Workup

  1. washThe organic layer is washed
  2. customdried
  3. concentrationconcentrated
  4. custompurified by flash chromatography (25% acetone in hexanes)

Sources & evidence

ORD record
ord-6a210aad632d403099b9e27309b55225
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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