Phosphorus trichloride → Benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2carboxylate

HRID 1493469Notes

Reaction equation

HRID 1493469 reaction equation
[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=O)[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].P(Cl)(Cl)[Cl:21]>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:21][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]

Participants

5

Reactant 2

HCID 24387Phosphorus trichlorideHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 12804728Benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl 1-azabicyclo[3.2.0]heptane-3,7-dione-2-carboxylate (26 mg, 0.1 mmol) in anhydrous DMF (0.5 ml) containing PCl3 (27 mg, 0.2 mmol) is kept at 25° C. for 5 hrs. The mixture is diluted with toluene (5 ml), washed with H2O (5×1 ml), 5% HCl (2 ml), 5% NaHCO3 (2 ml) and brine, dried with MgSO4, and filtered, Evaporation of the solvent in vacuo provides crude benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Workup

  1. washwashed with H2O (5×1 ml), 5% HCl (2 ml), 5% NaHCO3 (2 ml) and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-09130da9bebc49128b39d9b8c6126c8a
Source dataset
uspto-grants-1991_06
Patent number
US05021566

Reaction notes

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