Sodium Hydroxide → HCID 22633476, compound

HRID 398126Notes

Reaction equation

HRID 398126 reaction equation
C([O:3][C:4](=[O:38])[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[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=4[F:37])=[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.C1COCC1>[F:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([F:37])[C:30]=1[C:27]1[CH:28]=[CH:29][C:24]([C:20]2[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:38])=[O:3])=[CH:14][CH:13]=3)[N:19]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69871082HCID 69871082, compound

Product 1

HCID 22633476HCID 22633476, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Under nitrogen, 2-(4-{2-[2-(2′, 6′-difluoro-biphenyl-4-yl)-5-methyloxazol-4-yl]-ethoxy}-phenoxy)-2-methylpropionic acid ethyl ester (0.53 mmol) in ethanol (2.5 mL) and THF (2.5 mL) was treated with 2.0 N NaOH (2.0 mL). The reaction mixture was stirred at 55° C. for 1 h and concentrated in vacuo. The resulting slurry was suspended in ethyl acetate, acidified to pH 1 with 1 N HCl, and partitioned. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo to provide the product as a solid. 1H NMR (400 MHz, CDCl3) δ8.05 (d, J=8.0 Hz, 2H), 7.54 (d, J=8.0 Hz, 2H), 7.34-7.28 (m, 1H), 7.02-6.98 (m, 2H), 6.91-6.78 (m, 4H), 4.17 (t, J=6.6 Hz, 2H), 2.97 (t, J=6.6 Hz, 2H), 2.39 (s, 3H), 1.53 (s, 6H); MS (EI) 494.5 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4788265105e74e8897e17a5ce8a082b6
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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