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

HRID 2050391Notes

Reaction equation

HRID 2050391 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 was 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 was 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-b8be26f351c148ee940dadbe0827ce8b
Source dataset
uspto-grants-1980_04
Patent number
US04200572

Reaction notes

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