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

HRID 1664559Notes

Reaction equation

HRID 1664559 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. The mixture was stirred at room temperature for 2 hours. The mixture was adjusted to PH=3-4 under ice bath, and extracted with EtOAc (3×). The combined organic phases were washed with water and brine, dried over Na2SO4 and concentrated to yield the desired product (4.8 g, 98%) as colorless oil. LCMS calculated for C12H13N2O3 (M+H): 233.1. found 233.0.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2192165e85c742eeab1e109f6983a6ee
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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