Sodium Hydroxide → HCID 22633468, compound

HRID 398135Notes

Reaction equation

HRID 398135 reaction equation
C([O:3][C:4](=[O:36])[C:5]([CH3:35])([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]([C:29]4[CH:30]=[N:31][CH:32]=[N:33][CH:34]=4)=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+]>C(O)C.C1COCC1>[CH3:35][C:5]([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:24]=[CH:25][C:26]([C:29]4[CH:30]=[N:31][CH:32]=[N:33][CH:34]=4)=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)([CH3:6])[C:4]([OH:36])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69871063HCID 69871063, compound

Product 1

HCID 22633468HCID 22633468, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Under nitrogen, 2-methyl-2-(4-{2-[5-methyl-2-(4-pyrimidin-5-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-propionic 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 yield the desired product. 1H NMR (400 MHz, CDCl3) δ9.23 (s, 1 H), 9.20 (s, 2 H), 8.16 (d, 2 H), 7.65 (d, 2 H), 6.86 (d, 2 H), 6.76 (d, 2 H), 4.20 (t, 2 H), 3.00 (t, 2 H), 2.39 (s, 3 H), 1.48 (s, 6 H); MS (EI) 460.2 (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-bb426b5b5dc84cd9a3be9fe12af5e9ef
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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