Pyridine → 3-Azido-4-(2-trifluoroacetoxyethyl)azetidin-2-one

HRID 1154911Notes

Reaction equation

HRID 1154911 reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=O.[N:14]([CH:17]1[CH:20](CCO)[NH:19][C:18]1=[O:24])=[N+:15]=[N-:16].N1C=CC=CC=1>C(Cl)Cl>[N:14]([CH:17]1[CH:20]([CH2:2][CH2:3][O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])[NH:19][C:18]1=[O:24])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 155923893-Azido-4-(2-hydroxyethyl)-2-azetidinone

Product 1

HCID 543317643-Azido-4-(2-trifluoroacetoxyethyl)azetidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (0.2 mol) is added dropwise to an ice-cold, stirred solution of 3-azido-4-(2-hydroxyethyl)-azetidin-2-one (0.2 mol) and pyridine (0.21 mol) in methylene chloride (200 ml). The solution is stirred for 15 more min. at room temperature (25° C.), then washed with water, dried with magnesium sulfate, and filtered. Evaporation of the methylene chloride under vacuum leaves 3-azido-4-(2-trifluoroacetoxyethyl)azetidin-2-one.

Workup

  1. washat room temperature (25° C.), then washed with water
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customEvaporation of the methylene chloride under vacuum

Sources & evidence

ORD record
ord-3993c06d10d34cd0bcb9ce30aae4000f
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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