Potassium Carbonate → Benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1493475Notes

Reaction equation

HRID 1493475 reaction equation
[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=[O:9])[CH:2]2[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].FC(S(O[CH2:28][CH2:29][N:30]=[N+:31]=[N-:32])(=O)=O)(F)F.C(=O)([O-])[O-].[K+].[K+]>C=C.CCOCC>[N:30]([CH2:29][CH2:28][O:9][C:3]1[CH2:4][CH:5]2[N:1]([C:7](=[O:8])[CH2:6]2)[C:2]=1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[N+:31]=[N-:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylateHCID 198314892-Azidoethyl trifluoromethanesulfonate

Product 1

HCID 15136300Benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6325EthyleneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of benzyl 1-azabicyclo[3.2.0]heptane-3,7-dione-2-carboxylate (26 mg) and 2-azidoethyl trifluoromethyl sulfonate (26 mg) in anhydrous acetene (0.5 ml) containing powdered potassium carbonate (28 mg) is stirred at 25° C. in a capped flask for 2 hrs. The mixture is diluted with anhydrous ether (5 ml) and filtered. The filtrate is washed with water (2 ml) and brine, dried with MgSO4, filtered, and evaporated in vacuo. The residue is purified by plc on a silica gel GF plate to afford benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationfiltered
  2. washThe filtrate is washed with water (2 ml) and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue is purified by plc on a silica gel GF plate

Sources & evidence

ORD record
ord-c6a8d9e5f3fb45b3ad2af8d008854ae2
Source dataset
uspto-grants-1991_06
Patent number
US05021566

Reaction notes

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