Ethyl Acetate → cis-3-Azido-4-oxo-2-azetidinylmethyl bromide

HRID 1112344Notes

Reaction equation

HRID 1112344 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][C@H:6]1[C@@H:9]([N:10]=[N+:11]=[N-:12])[C:8](=[O:13])[NH:7]1)(=O)=O.[Li+].[Br-:22].C(OCC)(=O)C>CN(C)C=O>[N:10]([C@H:9]1[C:8](=[O:13])[NH:7][C@H:6]1[CH2:5][Br:22])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 82050Lithium BromideHCID 86734335HCID 86734335, compound

Product 1

HCID 86736078cis-3-Azido-4-oxo-2-azetidinylmethyl bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A degassed solution of cis-3-azido-4-oxo-2-azetidinylmethyl tosylate (0.41 g, 1.4 mmol) in dimethylformamide (5 ml) was heated to 90° with LiBr (0.43 g, 5 mmol) for 4 hours. The reaction was poured into ethyl acetate and washed copiously with water. The dried solution was evaporated to give the title compound.

Workup

  1. washwashed copiously with water
  2. customThe dried solution was evaporated

Sources & evidence

ORD record
ord-7f9dc7402b6f40cfba065dd4816442d6
Source dataset
uspto-grants-1978_10
Patent number
US04122086

Reaction notes

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