Phosphorus oxychloride → Ethyl 3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoate

HRID 1820186Notes

Reaction equation

HRID 1820186 reaction equation
[C:1]([NH:9][NH:10][C:11]([NH:13][CH:14]([CH:20]([CH3:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>ClCCCl>[CH3:21][CH:20]([CH3:22])[CH:14]([NH:13][C:11]1[O:12][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][N:10]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57889428Ethyl 2-(2-benzoylhydrazinecarboxamido)-3-methylbutanoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of crude ethyl 2-(2-benzoylhydrazinecarboxamido)-3-methylbutanoate (assumed 5 mmol) in DCE (10 ml) was added POCl3 (1.5 g, 10 mmol). Upon completion of addition, the reaction was heated at 75-80° C. overnight. After this time, the excess solvent and POCl3 were removed in vacuo. The resulting remains were dissolved in EtOAc (75 ml) and washed sequentially with sat. aqueous NaHCO3 (2×25 mL) solution and sat. aqueous NaCl (25 mL) solution and dried over MgSO4. The solvent was removed in vacuo to give ethyl 3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoate in greater than 90% purity by LCMS; m/z (290, M+1).

Workup

  1. additionUpon completion of addition
  2. customAfter this time, the excess solvent and POCl3 were removed in vacuo
  3. dissolutionThe resulting remains were dissolved in EtOAc (75 ml)
  4. washwashed sequentially with sat. aqueous NaHCO3 (2×25 mL) solution and sat. aqueous NaCl (25 mL) solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-df7aa3d5d5e449ef8f4bc2a89b005e96
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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