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

HRID 1016116Notes

Reaction equation

HRID 1016116 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-5cfc4ae756c0489abb0724627499f13d
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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