Sodium Hydroxide → 5-[5-(2-Methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoic acid

HRID 1616574Notes

Reaction equation

HRID 1616574 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[O:15][N:14]=[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[N:12]=1>CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[O:15][N:14]=[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59167762Methyl 5-[5-(2-methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoate

Product 1

HCID 684879075-[5-(2-Methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoic acidYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add a solution of 2 N sodium hydroxide (20 mL) to a solution of methyl 5-[5-(2-methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoate (3.4 g, 11 mmol) in methanol (50 mL) at room temperature under nitrogen and stir the mixture for 3.5 h. Remove the solvent under reduced pressure, dilute the residue with water (200 mL) and wash with diethyl ether (200 mL). Adjust the aqueous layer to pH 1 with 1 N HCl and collect the solids by vacuum filtration to afford 5-[5-(2-methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoic acid (2.2 g, 72%): APCI MS m/z 275 [C14H16N2O4—H]−.

Workup

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with water (200 mL)
  3. washwash with diethyl ether (200 mL)
  4. customcollect the solids
  5. filtrationby vacuum filtration

Sources & evidence

ORD record
ord-66536647728342c383c8224481697800
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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