Potassium Hydroxide → HCID 68489927, compound

HRID 1443669Notes

Reaction equation

HRID 1443669 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[NH:17][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:15][CH2:14]1)C>O.C1COCC1.CO>[C:18]1([C:16]2[NH:17][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:24])=[O:5])[CH2:14][N:15]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 68492649HCID 68492649, compound

Product 1

HCID 68489927HCID 68489927, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of potassium hydroxide (1.8 g, 32 mmol) in water (70 mL) to a solution of 7-(5-phenyl-4H-[1,3,4]triazol-3-yl)heptanoic acid ethyl ester (4.9 g, 16 mmol) in THF (50 mL) and methanol (50 mL) at room temperature under nitrogen and heat the mixture at reflux for 3 hours. Remove the solvent under reduced pressure, dilute the residue with water (200 mL) and wash with ethyl acetate (200 mL). Adjust the pH of the aqueous layer to 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 7-(5-phenyl-4H-[1,3,4]triazol-3-yl)heptanoic acid (4.4 g, 99%). APCI mass spectrum m/z 273 [C15H19N3O2]−.

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux for 3 hours
  3. customRemove the solvent under reduced pressure
  4. additiondilute the residue with water (200 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-ea919167a77043eeae240f6f59c668aa
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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