Sodium Hydroxide → HCID 22633447, compound

HRID 398156Notes

Reaction equation

HRID 398156 reaction equation
C([O:3][C:4](=[O:39])[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]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[C:11]([CH2:36][CH2:37][CH3:38])[CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24]([C:20]2[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:39])=[O:3])=[CH:10][C:11]=3[CH2:36][CH2:37][CH3:38])[N:19]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69869841HCID 69869841, compound

Product 1

HCID 22633447HCID 22633447, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2-{4-[2-(2-biphenyl-4-yl-5-methyloxazol-4-yl)ethoxy]-3-propylphenoxy}-2-methylpropionic acid ethyl ester, (0.57 mmol) in ethanol (10 mL) was treated with 2.5 N aqueous NaOH (1.1 mL), and heated at 55° C. for 2 h. The reaction was cooled to ambient temperature and concentrated down to near dryness. The residue was then diluted with ethyl acetate (40 mL) and water (20 mL) and acidified to pH=1 with 1N aqueous HCl. The organic layer was washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give 2-{4-[2-(2-biphenyl-4-yl-5-methyloxazol-4-yl)ethoxy]-3-propylphenoxy}-2-methylpropionic acid 1H NMR (400 MHz, CDCl3) δ8.06 (d, J=8.3 Hz, 2H), 7.67 (d, J=8.3 Hz, 2H), 7.63 (d, J=8.3 Hz, 2H), 7.46 (t, J=7.6 Hz, 2H), 7.32 (t, J=7.3 Hz, 1H), 6.72 (s, 3H), 4.21 (t, J=6.4 Hz, 2H), 3.02 (t, J=6.1 Hz, 2H), 2.50 (t, J=7.6 Hz, 2H), 2.41 (s, 3H), 1.52 (s, 6H), 1.31-1.24 (m, 2H), 0.88 (t, J=7.3 Hz, 3H); MS (ES) m/e 500 (M+1).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated down to near dryness
  3. additionThe residue was then diluted with ethyl acetate (40 mL) and water (20 mL)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bb9fbcdfd4841e5b06742bc5d4af6df
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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