Cesium carbonate → HCID 69354707, compound

HRID 348279Notes

Reaction equation

HRID 348279 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]3[O:37][C:38]([CH3:54])=[C:39]([CH2:41][CH2:42]OS(C4C=CC(C)=CC=4)(=O)=O)[N:40]=3)[CH:31]=2)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:42][CH2:41][C:39]2[N:40]=[C:36]([C:32]3[CH:31]=[C:30]([C:27]4[CH:26]=[CH:25][C:24]([F:23])=[CH:29][CH:28]=4)[CH:35]=[CH:34][CH:33]=3)[O:37][C:38]=2[CH3:54])=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateHCID 86593516HCID 86593516, compound

Product 1

HCID 69354707HCID 69354707, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

3-(4-Hydroxyphenyl)-2-methyl-2-phenoxypropionic acid ethyl ester (495 mg, 1.7 mmol) (see Ex. 1, Part C), toluene-4-sulfonic acid 2-[2-(4′-fluorobiphenyl-3-yl)-5-methyloxazol-4-yl]ethyl ester (2.2 mmol) and Cs2CO3 (700 mg, 2.2 mmol) are combined in anhydrous DMF (25 mL) and stirred for 16 h at 55° C. under an atmosphere of nitrogen. The mixture was then cooled and diluted with ethyl acetate (100 mL), and washed with water then brine. The organic layer was dried with Na2SO4 and concentrated in vacuo to a viscous yellow oil. The residue was purified by flash column chromatography (100 g silica, 60×15 mL fractions, gradient elution 0–20% ethyl acetate in hexanes) to provide the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.18–8.17 (m, 1H), 7.96–7.94 (m, 1H), 7.62–7.57 (m, 3H), 7.51–7.47 (m, 1H), 7.23–7.11 (m, 2H), 7.16–7.11 (m, 3H), 6.98–6.94 (m, 1H), 6.84–6.81 (m, 4H), 6.78–6.75 (m, 1H), 4.24 (t, J=6.4 Hz, 2H), 4.20 (q, J=7.2 Hz, 2H), 3.26 (d, J=14.0 Hz, 1H), 3.10 (d, J=14.0 Hz, 1H), 2.99 (t, J=6.4 Hz, 2H), 2.40 (s, 3H), 1.38 (s, 3H), 1.21 (t, J=7.2 Hz, 3H); MS (EI) 580.2 (M+)+.

Workup

  1. temperatureThe mixture was then cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried with Na2SO4
  4. concentrationconcentrated in vacuo to a viscous yellow oil
  5. customThe residue was purified by flash column chromatography (100 g silica, 60×15 mL fractions, gradient elution 0–20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c0cd3022f7e44a5991c7c967e9837711
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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