Pyridine → 4-Acetoxy-3-phenylacetamidoazetidin-2-one

HRID 127166Notes

Reaction equation

HRID 127166 reaction equation
[C:1]([O:4][CH:5]1[N:8](C(C(OC)=O)=C(C)C)[C:7](=[O:17])[CH:6]1[NH:18][C:19](=[O:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.[Mn]([O-])(=O)(=O)=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O.O>[C:1]([O:4][CH:5]1[NH:8][C:7](=[O:17])[CH:6]1[NH:18][C:19](=[O:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24477Sodium ThiosulfateHCID 516875Potassium PermanganateHCID 129077594-Acetoxy-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamidoazetidin-2-one

Product 1

HCID 111291064-Acetoxy-3-phenylacetamidoazetidin-2-oneYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-acetoxy-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamidoazetidin-2-one (709 mg, 1.9 mmol [R. J. Stoodley and N. R. Whitehouse, J. Chem. Soc., Perkin I, 32 (1973).] in 5 ml dimethylformamide, 5 ml pyridine and 1 ml water at 0° C. in an ice-water bath is added 497 mg (3.15 mmol) solid potassium permanganate. The mixture is stirred at 0° C. under a nitrogen atmosphere for 1.0 hour. The mixture is treated with sufficient aqueous sodium thiosulfate to destroy the excess permanganate and is diluted with ethylacetate. The mixture is filtered and the filtrate is partitioned between ethylacetate and dilute aqueous hydrochloric acid. The organic phase is separated and is washed successively with dilute aqueous sodium bicarbonate and brine. The organic phase is dried (MgSO4), filtered, and evaporated. The residue is purified by plate layer chromatography [1 development φH-EtOAc (1:1)] to give 95.1 mg (19%) of 1; nmr (CDCl3) 2.03, 3H(s); 3.5, 2H(s); 4.67; 1H(dd, J=1 Hz,7 Hz); 5.73, 1H(d, J=1 Hz); 7.17, 6H(s); 7.53, 1H(bs). ##STR29##

Workup

  1. customto destroy the excess permanganate
  2. additionis diluted with ethylacetate
  3. filtrationThe mixture is filtered
  4. customthe filtrate is partitioned between ethylacetate and dilute aqueous hydrochloric acid
  5. customThe organic phase is separated
  6. washis washed successively with dilute aqueous sodium bicarbonate and brine
  7. dry with materialThe organic phase is dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by plate layer chromatography [1 development φH-EtOAc (1:1)]

Sources & evidence

ORD record
ord-572910e64d1541efb9e504989c0342c0
Source dataset
uspto-grants-1981_03
Patent number
US04255330

Reaction notes

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