Phosphorus trichloride → Benzyl 6-azido-3-chloro-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

HRID 1154922Notes

Reaction equation

HRID 1154922 reaction equation
P(Cl)(Cl)[Cl:2].[N:5]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][C:11](=O)[CH:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[N+:6]=[N-:7]>CN(C)C=O.C1(C)C=CC=CC=1>[N:5]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][C:11]([Cl:2])=[C:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[N+:6]=[N-:7]

Participants

5

Reactant 2

HCID 24387Phosphorus trichlorideHCID 20563654Benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate

Product 1

HCID 20563652Benzyl 6-azido-3-chloro-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Phosphorus trichloride (1 mmol) is added to a solution of benzyl 6-azido-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (0.5 mmol) in anhydrous dimethylformamide (2.5 ml) and the mixture is left to stand at room temperature. After 5 hr, the mixture is diluted with toluene, washed with water, 1 N hydrochloric acid, 5% sodium bicarbonate solution, and brine, dried over magnesium sulfate, and filtered. Evaporation of the solvent under vacuum yields benzyl 6-azido-3-chloro-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate.

Workup

  1. waitthe mixture is left
  2. customto stand at room temperature
  3. washwashed with water, 1 N hydrochloric acid, 5% sodium bicarbonate solution, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customEvaporation of the solvent under vacuum

Sources & evidence

ORD record
ord-d4e0ba69f3eb4745b8860f8c9dfe5d72
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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