Cesium carbonate → HCID 69352826, compound

HRID 348294Notes

Reaction equation

HRID 348294 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][CH2:15][CH3:16])[CH:8]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:32]1([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:37]=[CH:36][CH:35]=[C:34]([C:38]2[O:39][C:40]([CH3:56])=[C:41]([CH2:43][CH2:44]OS(C3C=CC(C)=CC=3)(=O)=O)[N:42]=2)[CH:33]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:44][CH2:43][C:41]2[N:42]=[C:38]([C:34]3[CH:33]=[C:32]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[CH:37]=[CH:36][CH:35]=3)[O:39][C:40]=2[CH3:56])=[C:9]([CH2:14][CH2:15][CH3:16])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 20823153HCID 20823153, compoundHCID 58979436Toluene-4-sulfonic acid 2-(2-biphenyl-3-yl-5-methyloxazol-4-yl)ethyl ester

Product 1

HCID 69352826HCID 69352826, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 3-(4-hydroxy-3-propylphenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (266 mg, 1.0 mmol) in DMF (10 mL) was treated with cesium carbonate (407 mg, 1.25 mmol) and toluene-4-sulfonic acid 2-(2-biphenyl-3-yl-5-methyl-oxazol-4-yl)-ethyl ester (520 mg, 1.20 mmol) (see Ex. 2, Part F) and then heated at 55° C. for 18 h. After cooling to ambient temperature, the mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and then the organic phases were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (100 mL SiO2, hexanes to 30% ethyl acetatelhexanes) to provide the desired product (315 mg, 60%) as a clear, colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.68–7.63 (m, 3H), 7.51 (t, J=7.6 Hz, 1H), 7.46 (t, J=8.0 Hz, 2H), 7.38 (t, J=7.2 Hz, 1H), 7.25–7.21 (m, 2H), 7.04–6.96 (m, 3H), 6.85–6.69 (m, 3H), 4.26 (t, J=6.4 Hz, 2H), 4.21 (q, J=6.8 Hz, 2H), 3.26 (A of AB, J=13.6 Hz, 1H), 3.09 (B of AB, J=13.6 Hz, 1H), 3.01 (t, J=6.4 Hz, 2H), 2.54 (t, J=7.6 Hz, 2H), 2.41 (s, 3H), 1.54 (sextet, J=7.6 Hz, 2H), 1.41 (s, 3H), 1.23 (t, J=6.8 Hz, 3H), 0.91 (t, J=7.2 Hz, 3H); MS (EI) 604.3 (M+H)+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (100 mL SiO2, hexanes to 30% ethyl acetatelhexanes)

Sources & evidence

ORD record
ord-ba86ed87d2f644eab28058572c2282da
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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