Sodium Hydroxide → HCID 43515007, compound

HRID 1616559Notes

Reaction equation

HRID 1616559 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[N:11]=1>CO>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[N:11]=[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:23])=[O:4])[O:14][N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59167745HCID 59167745, compound

Product 1

HCID 43515007HCID 43515007, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 2 N sodium hydroxide (20 mL) to a solution of 5-[3-(2-methoxyphenyl)-[1,2,4]oxadiazol-5-yl]pentanoic acid methyl ester (4.00 g, 13 mmol) in methanol (100 mL) at room temperature under nitrogen and stir the mixture for 3 hours. Remove the solvent under reduced pressure, dilute the residue with water (200 mL) and wash with diethyl ether (200 mL). Adjust the aqueous layer to pH 1 with 2 N HCl and collect the solids by vacuum filtration to afford 5-[3-(2-methoxyphenyl)-[1,2,4]oxadiazol-5-yl]pentanoic acid (3.65 g, 99%). APCI mass spectrum m/z 275 [C14H16N2O4—H]−.

Workup

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with water (200 mL)
  3. washwash with diethyl ether (200 mL)
  4. customcollect the solids
  5. filtrationby vacuum filtration

Sources & evidence

ORD record
ord-345f38180bf44df28ec4452563207ec9
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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