HCID 131714275, compound → HCID 86740200, compound

HRID 371226Notes

Reaction equation

HRID 371226 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.[N:18]([C@H:21]1[C@H:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]([S:31]([O-:34])(=[O:33])=[O:32])[C:22]1=[O:35])=[N+]=[N-]>CO.[Pt]=O>[NH2:18][C@H:21]1[C@H:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:23]([S:31]([OH:34])(=[O:32])=[O:33])[C:22]1=[O:35]

Participants

4

Reactant 1

HCID 131714275HCID 131714275, compound

Product 1

HCID 86740200HCID 86740200, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A solution of (±)-(trans)-3-azido-2-oxo-4-phenyl-1-azetidinesulfonic acid, tetrabutylammonium salt (see example 181) in 4 ml of methanol is hydrogenated over 30 mg of platinum oxide at 1 atmosphere and room temperature. After 15 minutes, the system is evacuated and fresh hydrogen is introduced. After an additional 45 minutes the reaction is complete, and the system is flushed with nitrogen. After several days at room temperature in dichloromethanemethanol (4:1, 200 ml) catalyst aggregation is complete and filtration is accomplished. The filtrate is concentrated in vacuo to 18 ml and 0.2 ml of 97% formic acid is added. After cooling at 5° C. for several hours the resulting solid is filtered and washed with dichloromethane to afford, after drying, 150 mg of the title compound as a solid.

Workup

  1. customthe system is evacuated
  2. additionfresh hydrogen is introduced
  3. waitAfter an additional 45 minutes the reaction is complete
  4. customthe system is flushed with nitrogen
  5. waitAfter several days at room temperature in dichloromethanemethanol (4:1, 200 ml) catalyst aggregation is complete
  6. filtrationfiltration
  7. concentrationThe filtrate is concentrated in vacuo to 18 ml and 0.2 ml of 97% formic acid
  8. additionis added
  9. filtrationis filtered
  10. washwashed with dichloromethane
  11. customto afford
  12. customafter drying

Sources & evidence

ORD record
ord-57e57c828b274c28a02d117d3b8c85fc
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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