Phosphate → HCID 53833434, compound

HRID 2058192Notes

Reaction equation

HRID 2058192 reaction equation
[C:1]([O:4][CH:5]1[N:8](C(C(OCC2C=CC=CC=2)=O)=C(C)C)[C:7](=[O:23])[C:6]1([O:34][CH3:35])[NH:24][C:25](=[O:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:3])[CH3:2].P([O-])([O-])([O-])=O.[O-][Mn](=O)(=O)=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.O.CCOC(C)=O>[C:1]([O:4][CH:5]1[NH:8][C:7](=[O:23])[C:6]1([O:34][CH3:35])[NH:24][C:25](=[O:33])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1061PhosphateHCID 24477Sodium ThiosulfateHCID 516875Potassium Permanganate2×HCID 54128149HCID 54128149, compound

Product 1

HCID 53833434HCID 53833434, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirred solution of 240 mg (0.5 mmol) of azetidinone prepared in Example 1 in 8 ml of 8:1 acetone-water and 2 drops of pH 7 0.1 N phosphate buffer at 25° C. is added 79 mg (0.5 mmol) of solid KMnO4. The mixture is stirred under N2 at 25° for 8 minutes and an additional 79 mg (0.5 mmol) of KMnO4 is then added. The mixture is stirred further for 45 minutes and diluted with EtOAc. The mixture is treated with sufficient aqueous sodium thiosulfate to destroy any remaining permanganate. The mixture is then filtered through celite and washed thoroughly with ethyl acetate. The filtrate is partitioned between EtOAc/brine and the organic phase is separated, dried (MgSO4), filtered and evaporated. Purification of the residue by plate layer chromatography affords 4-acetoxy-3-methoxy-3-phenylacetamido-azetidin-2-one (1). ##STR39##

Workup

  1. stirringThe mixture is stirred further for 45 minutes
  2. customto destroy any remaining permanganate
  3. filtrationThe mixture is then filtered through celite
  4. washwashed thoroughly with ethyl acetate
  5. customThe filtrate is partitioned between EtOAc/brine
  6. customthe organic phase is separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customPurification of the residue by plate layer chromatography

Sources & evidence

ORD record
ord-bc7168f576a84c10a0351ff18e495f3c
Source dataset
uspto-grants-1980_07
Patent number
US04215124

Reaction notes

Loading…