Sodium Hydroxide → HCID 22261200, compound

HRID 898438Notes

Reaction equation

HRID 898438 reaction equation
C([O:3][C:4](=[O:37])[C:5]([CH3:36])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+]>CCO>[CH3:36][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:12][CH:13]=1)([CH3:6])[C:4]([OH:37])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23590026HCID 23590026, compound

Product 1

HCID 22261200HCID 22261200, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 2-methyl-2-(4-{2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-propionic acid ethyl ester (0.316 g, 0.614 mmol) was combined with 5 N NaOH (0.61 mL, 3.05 mmol) in absolute EtOH (20 mL) and heated to reflux for 3 h. The reaction mixture was cooled, filtered through hyflo, and the solvent removed in vacuo from the filtrate. The residue was acidified with 1 N HCl (3.2 mL) and then extracted with EtOAc and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to give 0.282 g of crude 2-methyl-2-(4-{2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-propionic acid. Approximately ⅓ of this material was purified by LCMS to afford 0.014 g of analytically pure 2-methyl-2-(4-{2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-propionic acid: 1H NMR (500 MHz, CDCl3) δ 7.90 (d, 2H, J=8.80 Hz), 7.36-7.32 (m, 2H), 7.18-7.12 (m, 1H), 7.03-6.99 (m, 3H), 6.88-6.86 (m, 2H), 6.79-6.77 (m, 3H), 4.16 (t, 2H, J=6.84 Hz), 2.94 (t, 2H, J=6.84 Hz), 2.34 (s, 3H), 1.44 (s, 6H). HRMS (ES+) m/z exact mass calcd for C28H28NO6 474.1917, found 474.1929.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through hyflo
  5. customthe solvent removed in vacuo from the filtrate
  6. extractionextracted with EtOAc and water
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6e5182b438494a7cbfd82a6c4c37d0cd
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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