Ethyl Acetate → HCID 56617225, compound

HRID 580064Notes

Reaction equation

HRID 580064 reaction equation
[CH3:1][O:2][C:3]([C@H:5]([N:11]1[C@H:14]([CH:15]=CC2C=CC=CC=2)[C@H:13]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C:12]1=[O:34])[CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[Mn]([O-])(=O)(=O)=[O:36].[K+].S([O-])([O-])(=[O:43])=S.[Na+].[Na+].[C:48](OCC)(=[O:50])C>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.O>[CH3:1][O:2][C:3]([C@H:5]([N:11]1[C@@H:14]([C:15]([O:50][CH3:48])=[O:43])[C@H:13]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[C:12]1=[O:34])[CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[CH2:27]([O:26][C:24]([NH:23][C@H:13]1[C@H:14]([C:15]([O:50][CH3:48])=[O:36])[NH:11][C:12]1=[O:34])=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 516875Potassium PermanganateHCID 56635270HCID 56635270, compound

Product 2

HCID 56617225HCID 56617225, compoundHCID 56622500HCID 56622500, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

With stirring at room temperature, a solution of 0.467 g of (3S,4R)-1-[(1R)-1,2-di(methoxycarbonyl)ethyl]-3-benzyloxycarbonylamino-4-styryl-2-azetidinone in 20 ml of ethyl acetate and 0.068 g of n-Bu4NHSO4 are added to a solution of 0.79 g of potassium permanganate in 20 ml of water, and the mixture is stirred at room temperature for 2 hours. To the reaction mixture is added an aqueous solution of sodium thiosulfate and the mixture is passed through a Celite layer and washed with water and ethyl acetate. The aqueous layer is separated, adjusted to pH 1.5 with 5N hydrochloric acid and extracted twice with ethyl acetate. The extract is washed with aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is purified by silica gel column chromatography [eluent: ethyl acetate-n-hexane (1:1 to 2:1, v/v)] to give 0.205 g of (3S,4R)-1-[(1R)-1,2 -di(methoxycarbonyl)ethyl]-3-benzyloxycarbonylamino-4-methoxycarbonyl-2-azetidinone and 23 mg of (3S,4R)-3-benzyloxycarbonylamino-4-methoxycarbonyl-2-azetidinone.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. washwashed with water and ethyl acetate
  3. customThe aqueous layer is separated
  4. extractionextracted twice with ethyl acetate
  5. washThe extract is washed with aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is then distilled off under reduced pressure
  8. customthe residue is purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-250686acc53d462298555434f67588ac
Source dataset
uspto-grants-1988_06
Patent number
US04751299

Reaction notes

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