Methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoate → 5-Phenyl-1,3,4-oxadiazole-2-propionic acid

HRID 2368602Notes

Reaction equation

HRID 2368602 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[OH-].[Na+].CO>[C:1]1([C:7]2[O:11][C:10]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 57600262Methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoate

Product 1

HCID 71306335-Phenyl-1,3,4-oxadiazole-2-propionic acidYield 114.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoate (600 mg, 2.0 mmol) in 1 M of aqueous NaOH (10 mL) and Methanol (10 mL) was stirred at room temperature overnight. The reaction solution was adjusted to pH 5 and extracted with ethyl acetate three times. The combined organic layers were dried, filtered and concentrated to yield the desired product (0.50 g, 83%). LCMS calculated for C11H11N2O3 (M+H): 219.1. Found 219.1.

Workup

  1. extractionextracted with ethyl acetate three times
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e2d43013a03e4d45bf794e2c42fc999a
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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