Sodium Hydroxide → 3-Methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoic acid

HRID 1016117Notes

Reaction equation

HRID 1016117 reaction equation
[CH3:1][CH:2]([CH3:21])[CH:3]([NH:9][C:10]1[O:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:13][N:14]=1)[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>C1COCC1.CO.O>[CH3:1][CH:2]([CH3:21])[CH:3]([NH:9][C:10]1[O:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:13][N:14]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57888933Ethyl 3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoate

Product 1

HCID 578892573-Methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoic acidYield 50%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Crude ethyl 3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoate (assumed 5 mmol) was dissolved in a mixture of THF (10 ml) and MeOH (2 ml) and then treated dropwise (exothermic) with aqueous 1 N NaOH (6 mL) solution. The reaction was stirred for 1 h, diluted with H2O (50 mL) and then extracted with Et2O (1×50 mL). The aqueous layer was acidified to pH 3 with aqueous 1N HCl solution and then extracted with EtOAc (3×35 mL). The EtOAc extracts were combined, washed with sat. aqueous NaCl solution, dried (MgSO4) and the solvent was removed in vacuo to give 3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoic acid in 50-75% yield over 3 steps in purity >90% as judged by LCMS. MS found: 262 (M+H).

Workup

  1. extractionextracted with Et2O (1×50 mL)
  2. extractionextracted with EtOAc (3×35 mL)
  3. washwashed with sat. aqueous NaCl solution
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e4636c65bb2c410d8e871def10281314
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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