Sodium Hydroxide → 3-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid

HRID 2098326Notes

Reaction equation

HRID 2098326 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[O:25][C:26]([CH3:29])=[N:27][N:28]=3)=[CH:20][CH:19]=2)[CH:16]=1)[C:10]([O:12]C)=[O:11])[CH3:5].[OH-].[Na+]>C1COCC1.CO.O>[CH3:1][O:2][CH2:3][CH:4]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[O:25][C:26]([CH3:29])=[N:27][N:28]=3)=[CH:20][CH:19]=2)[CH:16]=1)[C:10]([OH:12])=[O:11])[CH3:5]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67514111Methyl 3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate2×

Product 1

HCID 669719313-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acidYield 77.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Methyl 3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate (Intermediate 2) (6.8 g, 17.08 mmol, 1 equiv.) in a mixture of THF and methanol (70 mL of 1:1 ratio) was treated with a solution of sodium hydroxide (2 g, 51.25 mmol, 3 equiv.) in water (50 mL) and the reaction mixture was stirred for 1 h. The resulting solution was concentrated in vacuo to remove THF and methanol, diluted with water (50 mL), extracted with EtOAc. The aqueous phase was cooled and acidified with 0.1 N HCl and extracted with DCM, combined organic extracts washed with brine, dried over Na2SO4 and concentrated in vacuo to give 3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid (5.1 g) as white solid.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customto remove THF and methanol
  3. additiondiluted with water (50 mL)
  4. extractionextracted with EtOAc
  5. temperatureThe aqueous phase was cooled
  6. extractionextracted with DCM
  7. washcombined organic extracts washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a5612cb0a5a469dbc98009b33c1d25d
Source dataset
uspto-grants-2013_05
Patent number
US08450494B2

Reaction notes

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