Potassium Carbonate → 3-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2-methoxy-phenoxy)-2-methyl-propionic Acid

HRID 585282Notes

Reaction equation

HRID 585282 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].C([O:9][C:10](=[O:29])[C:11]([CH3:28])([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1C)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)C.[C:30]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:35]=[CH:34][C:33]([C:36]2[O:37][C:38]([CH3:54])=[C:39]([CH2:41][CH2:42]OS(C3C=CC(C)=CC=3)(=O)=O)[N:40]=2)=[CH:32][CH:31]=1.[OH-].[Na+]>C(O)C>[C:30]1([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:35]=[CH:34][C:33]([C:36]2[O:37][C:38]([CH3:54])=[C:39]([CH2:41][CH2:42][O:19][C:16]3[CH:15]=[CH:14][C:13]([CH2:12][C:11]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:4][CH3:1])([CH3:28])[C:10]([OH:9])=[O:29])=[CH:18][CH:17]=3)[N:40]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12966835Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl esterHCID 208231553-(4-Hydroxy-phenyl)-2-methyl-2-o-tolyloxypropionic acid ethyl ester

Product 1

HCID 102098573-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2-methoxy-phenoxy)-2-methyl-propionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Potassium carbonate (0.078 g, 0.56 mmol) was added to a solution of 3-(4-Hydroxy-phenyl)-2-methyl-2-o-tolyloxypropionic acid ethyl ester and toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethyl ester in 4A sieve-dried ethanol (2 mL). The resultant mixture was stirred at 80° C. under an atmosphere of nitrogen for 18 h, then diluted with ethanol (2 mL). 5N NaOH (0.5 mL) was added, then the reaction mixture was refluxed for 2 h. The reaction mixture was concentrated in vacuo, diluted with 1N HCl, and extracted with CH2Cl2. The organic layer was dried through a Varian ChemElut cartridge, concentrated in vacuo, and purified by LCMS. 1H NMR (400 MHz, CDCl3): • 7.96-7.92 (m, 2H), 7.40 (t, 3H, J=3.13 Hz), 7.12 (d, 2H, J=6.65 Hz), 7.06 (t, 1H, J=7.82 Hz), 6.91 (t, 1H, J=7.82 Hz), 6.80 (t, 4H, J=6.65 Hz), 4.17 (t, 2H, J=6.65 Hz), 3.25 (d, 1H, J=14.08 Hz), 3.19 (d, 1H, J=14.08 Hz), 2.98 (t, 2H, J=6.65 Hz), 2.17 (s, 3H), 1.48 (s, 3H), 1.24 (s, 3H). MS [ES+] m/z exact mass calcd for C29H30NO5 472.2124, found 472.2129.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with 1N HCl
  4. extractionextracted with CH2Cl2
  5. customThe organic layer was dried through a Varian ChemElut cartridge
  6. concentrationconcentrated in vacuo
  7. custompurified by LCMS

Sources & evidence

ORD record
ord-140fd4496c454bbb8010cec5e9410155
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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