(3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone → HCID 15000239, compound

HRID 1196202Notes

Reaction equation

HRID 1196202 reaction equation
[Cl:1][CH2:2][C:3]([C@H:5]1[N:8](C(CC2C=CC(OC)=CC=2)CC2C=CC(OC)=CC=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])=[CH2:4]>C(#N)C.O.CO>[Cl:1][CH2:2][C:3]([C@H:5]1[NH:8][C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])=[CH2:4]

Participants

5

Reactant 1

HCID 67796056(3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Product 1

HCID 15000239HCID 15000239, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (320 g) in a mixture of acetonitrile and water (9 : 1) (3.8 liters) was added a solution of ceric ammonium nitrate (702 g) in a mixture of acetonitrile and water (9 : 1) (2 liters) at 5° C. or lower, followed by stirring for 30 minutes. The reaction mixture was diluted with water (5.2 liters) and extracted with ethyl acetate (3.4 liters). The aqueous layer was extracted with a mixture of ethyl acetate (1.7 liters), diethyl ether (1.7 liters) and benzene (1.7 liters). The combined extracts were washed successively with brine, 5l% sodium bicarbonate and brine, and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave an oily residue, which was dissolved in methanol (1.5 liters) with warming and allowed to cool gradually. After filtration to remove crystals, the filtrate was concentrated in vacuo to give an oily residue, which was purified by silica gel chromatography to yield (3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone.

Workup

  1. extractionextracted with ethyl acetate (3.4 liters)
  2. extractionThe aqueous layer was extracted with a mixture of ethyl acetate (1.7 liters), diethyl ether (1.7 liters) and benzene (1.7 liters)
  3. washThe combined extracts were washed successively with brine, 5l% sodium bicarbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration of the filtrate in vacuo
  6. customgave an oily residue, which
  7. temperaturewith warming
  8. temperatureto cool gradually
  9. filtrationAfter filtration
  10. customto remove crystals
  11. concentrationthe filtrate was concentrated in vacuo
  12. customto give an oily residue, which
  13. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-f666dc010bfb45928b69457a37f09327
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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