Sodium Hydroxide → HCID 22633436, compound

HRID 2229004Notes

Reaction equation

HRID 2229004 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[N:34]=[CH:33][CH:32]=[CH:31][N:30]=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:9]=[CH:10][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[N:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:12][CH:13]=1)([CH3:6])[C:4]([OH:36])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69872478HCID 69872478, compound

Product 1

HCID 22633436HCID 22633436, 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-2-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 1N 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) δ8.76 (d, 1H), 8.45 (d, 2H), 8.06 (d, 2H), 7.15 (t, 2H), 6.76 (d, 2H), 6.71 (d, 2H), 4.14 (t, 2H), 2.93 (t, 2H), 2.33 (s, 3H), 1.45 (s, 6H); MS (EI) 460.3 (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-b0b76b7e45964072ae4ee0513fced284
Source dataset
uspto-grants-2002_07
Patent number
US06417212B1

Reaction notes

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