Trifluoroacetic acid → cis-3-Amino-2-azidomethyl-4-oxoazetidine

HRID 1974184Notes

Reaction equation

HRID 1974184 reaction equation
[N:1]([CH2:4][C@H:5]1[C@@H:8]([NH:9]C(OC(C)(C)C)=O)[C:7](=[O:17])[NH:6]1)=[N+:2]=[N-:3].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:9][C@H:8]1[C:7](=[O:17])[NH:6][C@H:5]1[CH2:4][N:1]=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86734331cis-2-Azidomethyl-3-t-butoxycarbonylamino-4-oxoazetidine

Product 1

HCID 86734332cis-3-Amino-2-azidomethyl-4-oxoazetidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

cis-2-Azidomethyl-3-t-butoxycarbonylamino-4-oxoazetidine (ca. 1 g) is dissolved in 2 ml of methylene chloride and the solution is cooled to 0° and treated with 0.5 ml of trifluoroacetic acid for 30 minutes at 0°. The solution is washed with 5% aqueous sodium bicarbonate and extracted with dilute hydrochloric acid. The aqueous phase is neutralized and extracted with ethyl acetate. Evaporation of the solvent gives the title compound.

Workup

  1. temperaturethe solution is cooled to 0°
  2. washThe solution is washed with 5% aqueous sodium bicarbonate
  3. extractionextracted with dilute hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-eecd997b997e4601848a1256f0fb5a89
Source dataset
uspto-grants-1976_12
Patent number
US04000154

Reaction notes

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