Sodium Hydroxide → 3-(2-Methyl-4-{2-[5-methyl-2-(6-phenyl-pyridin-3-yl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid

HRID 854585Notes

Reaction equation

HRID 854585 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[N:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][CH:26]=3)[O:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH3:33].[OH-].[Na+]>C(O)C>[CH3:33][C:7]1[CH:8]=[C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[N:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][CH:26]=3)[O:18][C:19]=2[CH3:20])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([OH:34])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 694716873-(2-Methyl-4-{2-[5-methyl-2-(6-phenyl-pyridin-3-yl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester

Product 1

HCID 102882313-(2-Methyl-4-{2-[5-methyl-2-(6-phenyl-pyridin-3-yl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acidYield 56.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(2-Methyl-4-{2-[5-methyl-2-(6-phenyl-pyridin-3-yl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester (40 mg) in ethanol (1 mL) is added NaOH (5 N, 1.0 mL), stirred for 2 hr at 50° C., cooled to room temperature, concentrated. The residue is treated with ether and acidified by 5 N HCl, extracted with ether, concentrated. Reversed phase HPLC (water/acetonitrile) gave the title compound (22 mg). MS (ES): 443.3 (M++1).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue is treated with ether
  4. extractionextracted with ether
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0f23a31ba5ed4673ba4a4a966061cb81
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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