Dimethyl Sulfate → Benzyl 6-azido-3-methoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1154920Notes

Reaction equation

HRID 1154920 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].[C:23](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O.C(OCC)C>[N:1]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([O:22][CH3:23])=[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 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 20563654Benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate

Product 1

HCID 20563673Benzyl 6-azido-3-methoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

Benzyl 6-azido-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (1 mmol) is dissolved in anhydrous acetone (5 ml) and treated with powdered, anhydrous potassium carbonate (2 mmol). The resulting suspension is treated with dimethyl sulfate (1.2 mmol) and stirred vigorously at room temperature for several hours. The mixture is diluted with ethylether and filtered. The filtrate is washed with water and brine, dried and evaporated under vacuum to give benzyl 6-azido-3-methoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationfiltered
  2. washThe filtrate is washed with water and brine
  3. customdried
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-e69330479ea34926a5004bfb748fb203
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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