Chloroacetonitrile → 1-Cyanomethyl-3-(2-phenylacetamido)-2-azetidinone

HRID 1706513Notes

Reaction equation

HRID 1706513 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][NH:13][C:12]2=[O:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:17][C:18]#[N:19].[H-].[Na+].C(OCC)(=O)C>CN(C)C=O>[C:18]([CH2:17][N:13]1[CH2:14][CH:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]1=[O:15])#[N:19]

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 132120483-[(Phenylacetyl)amino]-2-azetidinone

Product 1

HCID 155923141-Cyanomethyl-3-(2-phenylacetamido)-2-azetidinoneYield 11.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-Phenylacetamido)-2-azetidinone (408 mg.) and 2-chloroacetonitrile (152 mg.) was dissolved in N,N-dimethylformamide (15 ml.), and to the solution was added sodium hydride (50% oily) (105 mg.) under stirring at ambient temperature, whereafter the reaction mixture was stirred for an hour at room temperature, and ethyl acetate (100 ml.) was added to the reaction mixture. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off from the solution under reduced pressure. The oily residue (0.25 g.) obtained was subjected to column chromatography using silica.gel. 1-Cyanomethyl-3-(2-phenylacetamido)-2-azetidinone (56.3 mg.) was obtained from fractions eluted with chloroform. Mp 108° to 109° C. (dec.).

Workup

  1. stirringwas stirred for an hour at room temperature
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off from the solution under reduced pressure
  5. customThe oily residue (0.25 g.) obtained

Sources & evidence

ORD record
ord-fd0a6d06aab644af9e0bbdc911847d64
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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