Sodium Hydroxide → HCID 54929886, compound

HRID 551755Notes

Reaction equation

HRID 551755 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:21])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:13][N:14]=1>C1COCC1.CO>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[O:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:21])=[O:4])=[N:14][N:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59027826Methyl 5-[5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl]pentanoate

Product 1

HCID 54929886HCID 54929886, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 2 N sodium hydroxide (20 mL) to a solution of 5-(5-pyridin-2-yl[1,3,4]oxadiazol-2-yl)pentanoic acid methyl ester (8.16 g, 31 mmol) in THF (60 mL) and methanol (20 mL) at room temperature under nitrogen and heat the mixture at reflux for 12 hours. Remove the solvent under reduced pressure, dilute the residue with water (500 mL), and wash with ethyl acetate (200 mL). Adjust the pH of the aqueous layer to pH 3 with concentrated HCl and extract with ethyl acetate (3×200 mL). Wash the combined organic extracts with brine (200 mL), dry over sodium sulfate, and remove the solvent under reduced pressure to afford 5-(5-pyridin-2-yl[1,3,4]oxadiazol-2-yl)pentanoic acid (2.05 g, 27%). APCI mass spectrum m/z 246 [C12H13N3O3+H]+.

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux for 12 hours
  3. customRemove the solvent under reduced pressure
  4. additiondilute the residue with water (500 mL)
  5. washwash with ethyl acetate (200 mL)
  6. extractionextract with ethyl acetate (3×200 mL)
  7. washWash the combined organic extracts with brine (200 mL)
  8. dry with materialdry over sodium sulfate
  9. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-0ccff0706eba443f8d77fc23b08f5a76
Source dataset
uspto-grants-2011_05
Patent number
US07947841B2

Reaction notes

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