Diethylaminoethyl chloride → Benzyl 6-azido-3-(2-diethylaminoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1154923Notes

Reaction equation

HRID 1154923 reaction equation
[N:1]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7](=[O:22])[CH:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[N+:2]=[N-:3].[H-].[K+].[CH2:25]([N:27]([CH2:30][CH2:31]Cl)[CH2:28][CH3:29])[CH3:26]>CN(C)C=O.C(OCC)(=O)C>[N:1]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([O:22][CH2:26][CH2:25][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 13364Diethylaminoethyl chlorideHCID 82127Potassium hydrideHCID 20563654Benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate

Product 1

HCID 20563664Benzyl 6-azido-3-(2-diethylaminoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

An ice-cold solution of benzyl 6-azido-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (1 mmol) in anhydrous dimethylformamide (1 ml) is added dropwise to an ice-cold mixture of potassium hydride (1 mmol) in anhydrous dimethylformamide (4 ml). After stirring for several minutes in the cold and under nitrogen, the mixture is treated with diethylaminoethyl chloride and stirred in the cold for 2 hr. The mixture is diluted with ethyl acetate, washed thoroughly with water and brine, dried over magnesium sulfate, and filtered. Evaporation of the solvent in vacuo gives benzyl 6-azido-3-(2-diethylaminoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. stirringstirred in the cold for 2 hr
  2. washwashed thoroughly with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-77c7d58e4f004ada8912ad709edb094f
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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