Sodium Hydroxide → 3-(3-Benzyl-1,2,4-oxadiazol-5-yl)propanoic acid

HRID 249785Notes

Reaction equation

HRID 249785 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[O:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59853830Methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoate

Product 1

HCID 398703933-(3-Benzyl-1,2,4-oxadiazol-5-yl)propanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoate (5.2 g, 21.1 mmole) in methanol (30 ml) was added 50 ml of 1N NaOH aqueous solution. The mixture was stirred at room temperature for 2 hours. After the reaction solution was adjusted to be acidic (pH=3-4) at 0° C., the reaction mixture was extracted with EtOAc 3 times. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated to give the desired product as colorless oil (4.8 g, 98%). LCMS calculated for C12H13N2O3 (M+H): 233.1. found: 233.1.

Workup

  1. customat 0° C.
  2. extractionthe reaction mixture was extracted with EtOAc 3 times
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-539165e47df84619a0672916ce4d1f3f
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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