Sodium Hydroxide → HCID 22261233, compound

HRID 1609943Notes

Reaction equation

HRID 1609943 reaction equation
C([O:3][C:4](=[O:37])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[CH:31]1([O:30][C:27]2[CH:26]=[CH:25][C:24]([C:20]3[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]4[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:37])=[O:3])=[CH:14][CH:13]=4)[N:19]=3)=[CH:29][CH:28]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69310449HCID 69310449, compound

Product 1

HCID 22261233HCID 22261233, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-{2-[2-(4-cyclohexyloxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (0.339 g, 0.667 mmol) in ethanol (40 mL) was treated with 5 N NaOH (0.8 mL) and the reaction heated to reflux for 1 h. The reaction mixture was cooled and the solvent removed in vacuo. The resultant oil was acidified with 1 N HCl and extracted with EtOAc and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 0.304 g (95%) of 2-(4-{2-[2-(4-cyclohexyloxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid. 1H NMR (500 MHz, CDCl3) δ 7.94-7.85 (m, 2H), 6.89-6.73 (m, 4H), 6.71 (d, 2H, J=9.28 Hz), 4.30-4.23 (m, 1H), 4.14-4.05 (m, 2H), 2.95-2.85 (m, 2H), 2.29 (s, 3H), 1.98-1.85 (m, 2H), 1.80-1.75 (m, 2H), 1.58-1.40 (m, 8H), 1.38-1.20 (m, 4H); HRMS (ES+) m/z exact mass calcd for C28H34NO6 480.2386, found 480.2381The following compound was prepared using tetrahydro-2H-pyran-4-ol:

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 1 h
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed in vacuo
  5. extractionextracted with EtOAc and water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-66971ff0864643a5b44af8bc15a7115d
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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