HCID 86734335, compound → cis-3-Amino-4-oxo-2-p-toluenesulfonyloxymethylazetidine

HRID 1974187Notes

Reaction equation

HRID 1974187 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[CH2:9][O:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])=[N+]=[N-]>C(O)(=O)C.[Zn]>[NH2:1][C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[CH2:9][O:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

4

Reactant 1

HCID 86734335HCID 86734335, compound

Product 1

HCID 86734334cis-3-Amino-4-oxo-2-p-toluenesulfonyloxymethylazetidine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (2.0 g, 0.03 mole) was slowly added with cooling to a solution of 5.0 g (0.011 mole) of cis-3-azido-4-oxo-2-p-toluenesulfonyloxymethylazetidine in 50 ml of 50% aqueous acetic acid. The reaction mixture was stirred for 30 minutes and filtered. The solids were washed with water and the filtrate was saturated with hydrogen sulfide, filtered and concentrated to near dryness. The residue was dissolved in ethyl acetate-water and the pH as adjusted to 8.0 by addition of sodium carbonate and sodium hydroxide solutions. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The extracts were combined, dried (MgSO4) and evaporated to dryness to give the title compound.

Workup

  1. filtrationfiltered
  2. washThe solids were washed with water
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate-water
  6. additionthe pH as adjusted to 8.0 by addition of sodium carbonate and sodium hydroxide solutions
  7. customThe layers were separated
  8. extractionthe aqueous phase was extracted twice with ethyl acetate
  9. dry with materialdried (MgSO4)
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-8a23f423e23e4491ada1da230d724182
Source dataset
uspto-grants-1976_12
Patent number
US04000154

Reaction notes

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