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

HRID 1039188Notes

Reaction equation

HRID 1039188 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-528ae8a4aaac4cdda7a9ac9db94a86e8
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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