Sodium Hydroxide → HCID 22633498, compound

HRID 2229054Notes

Reaction equation

HRID 2229054 reaction equation
C([O:3][C:4](=[O:40])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[C:11]([O:19][CH2:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])[CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[C:31]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:30]=[CH:29][C:28]([C:24]2[O:25][C:26]([CH3:27])=[C:22]([CH2:21][CH2:20][O:19][C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=3[CH2:15][CH2:16][CH2:17][CH3:18])[O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:40])=[O:3])[N:23]=2)=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69871842HCID 69871842, compound

Product 1

HCID 22633498HCID 22633498, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2-{3-[2-(2-biphenyl-4-yl-5-methyloxazol-4-yl)-ethoxy]-4-butylphenoxy}-2-methylpropionic acid ethyl ester (0.12 g, 0.258 mmol) in ethanol (3 mL) was treated with 2 N aqueous NaOH (0.64 mL), and heated at 55° C. for 8 h. The reaction was cooled to ambient temperature and concentrated down to near dryness. The residue was then diluted with ethyl acetate (25 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 a white solid (0.10 g, 88%). 1H NMR (400 MHz, CDCl3) δ8.05 (d, J=8.3 Hz, 2H), 7.69 (d, J=8.3 Hz, 2H), 7.64 (d, J=7.3 Hz, 2H), 7.47 (t, J=7.8 Hz, 2H), 7.38 (t, J=7.3 Hz, 1H), 7.00 (d, J=8.3 Hz, 1H), 6.81 (s, 1H), 6.50 (d, J=8.3 Hz, 1H), 4.24 (t, J=7.6 Hz, 2H), 2.93 (t, J=7.6 Hz, 2H), 2.40 (s, 3H), 1.60 (s, 6H), 1.51 (penta, J=7.6 Hz, 2H), 1.39-1.26 (m, 2H), 0.91 (t, J=7.3 Hz, 3H), MS (ES) m/e 514 (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 (25 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-52ecfa95ff394208988017fc9a36b215
Source dataset
uspto-grants-2002_07
Patent number
US06417212B1

Reaction notes

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