Cesium carbonate → HCID 68866820, compound

HRID 1985129Notes

Reaction equation

HRID 1985129 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:9][C:10](=[O:29])[C:11]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])([CH3:20])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH3:8].[CH3:30][O:31][C:32]1[CH:58]=[CH:57][C:35]([CH2:36][N:37]2[CH2:41][CH:40]([CH2:42][CH2:43]OS(C3C=CC(C)=CC=3)(=O)=O)[N:39]([CH3:55])[C:38]2=[O:56])=[CH:34][CH:33]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:7]([O:9][C:10](=[O:29])[C:11]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])([CH3:20])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:43][CH2:42][CH:40]2[CH2:41][N:37]([CH2:36][C:35]3[CH:57]=[CH:58][C:32]([O:31][CH3:30])=[CH:33][CH:34]=3)[C:38](=[O:56])[N:39]2[CH3:55])=[CH:17][CH:18]=1)[CH3:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 57719164Toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl esterHCID 577192632-(2-Fluorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 68866820HCID 68866820, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (8.23 g, 25.3 nmol) is added to a solution of 2-(2-Fluoro-phenoxy)-3-(4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester (2.68 g, 8.43 mmol) and toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl ester (3.88 g, 9.27 mmol) in DMF (30 mL). The resultant mixture is stirred at 65° C. under an atmosphere of nitrogen for 18 h, then diluted with ethyl acetate. The organic layer is washed with 1N HCl, water, and brine. The organic layer is dried, concentrated in vacuo, and purified by flash chromatography (17% acetone in hexanes) to provide the title compound (4.4 g, 93%). 1H NMR 400 MHz, CDCl3): δ 7.19-7.15 (m, 4H), 7.06-7.01 (m, 1H), 6.97-6.87 (m, 3H), 6.83 (d, 2H, J=8.6 Hz), 6.74 (d, 2H, J=8.6 Hz), 4.31, 4.27 (ABq 2H, J=14.8 Hz), 4.21, 4.17 (ABq, 2H, J=7.2 Hz), 3.96-3.92 (m, 2H), 3.76 (s, 3H), 3.60-3.53 (m, 1H), 3.33 (t, 1H, J=8.6 Hz), 3.25, 3.13 (ABq 2H, J=13.8 Hz), 2.994-2.83 (m, 2H), 2.82 (s, 3H), 2.24-2.16 (m, 1H), 1.89-1.80 (m, 1H), 1.37 (s, 3H), 1.22 (t, 3H, J=7.2 Hz). MS [EI+] 565 (M+H)+. Rf=0.56 in 50% acetone in hexanes.

Workup

  1. washThe organic layer is washed with 1N HCl, water, and brine
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (17% acetone in hexanes)

Sources & evidence

ORD record
ord-434652da35f6477fb294b6d7c6388db3
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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