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 348381Notes

Reaction equation

HRID 348381 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:9][C:10](=[O:30])[C:11]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])([CH3:20])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)C.[C:31]1([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:36]=[CH:35][C:34]([C:37]2[O:38][C:39]([CH3:55])=[C:40]([CH2:42][CH2:43]OS(C3C=CC(C)=CC=3)(=O)=O)[N:41]=2)=[CH:33][CH:32]=1.[OH-].[Na+]>C(O)C>[C:31]1([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:36]=[CH:35][C:34]([C:37]2[O:38][C:39]([CH3:55])=[C:40]([CH2:42][CH2:43][O:19][C:16]3[CH:15]=[CH:14][C:13]([CH2:12][C:11]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])([CH3:20])[C:10]([OH:9])=[O:30])=[CH:18][CH:17]=3)[N:41]=2)=[CH:33][CH:32]=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 588018243-(4-Hydroxyphenyl)-2-(2-methoxy-phenoxy)-2-methyl-propionic 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 (0.048 g, 0.35 mmol) was added to a solution of 3-(4-Hydroxy-phenyl)-2-(2-methoxy-phenoxy)-2-methyl-propionic 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): δ 8.05 (d, 2H, J=7.82 Hz), 7.70 (d, 2H, J=8.21 Hz), 7.62 (d, 2H, J=7.82 Hz), 7.45 (t, 2H, J=7.82 Hz), 7.39–7.36 (m, 1H), 7.19 (d, 2H, J=8.21), 6.88 (d, 1H, J=8.21 Hz), 6.84–6.80 (m, 3H), 6.63 (d, 1H, J=7.82 Hz), 4.22 (t, 2H, J=5.87 Hz), 3.82 (s, 3H), 3.30 (d, 1H, J=14.08 Hz), 3.08 (dd, 3H, J=9.78 Hz, 3.52 Hz), 2.43 (s, 3H), 1.30(s, 2H), 1.23 (s, 1H). MS [ES+] m/z exact mass calcd for C35H34NO6 564.2386, found 564.2407.

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-af49996c04bc46deab5800402dd0390b
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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