Water → HCID 13336393, compound

HRID 345645Notes

Reaction equation

HRID 345645 reaction equation
C([N:8]1[C@H:11]([CH2:12][Cl:13])[C@H:10]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[C:9]1=[O:25])C1C=CC=CC=1.[O-]S(OOS([O-])(=O)=O)(=O)=O.[K+].[K+].O.P(O)([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[C:15]1(=[O:24])[N:14]([C@H:10]2[C@@H:11]([CH2:12][Cl:13])[NH:8][C:9]2=[O:25])[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]12

Participants

6

Reactant 4

HCID 962WaterHCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, DibasicHCID 86743754HCID 86743754, compound

Product 1

HCID 13336393HCID 13336393, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 17.75 g of the product of Step B, 31 g of potassium peroxodisulfate, 110 ml of water and 160 ml of acetic acid was heated for 25 minutes with strong agitation in an oil bath at 120° C. and was then cooled to room temperature. 50 g of dipotassium phosphate were added to the mixture to adjust the pH to neutrality and was evaporated to dryness under reduced pressure. 250 ml of water and 150 ml of ethyl acetate were added to the residue and after stirring, sodium bicarbonate was added in small quantities until evolution of gas ceased. The mixture was filtered and the filtrate was rinsed with ethyl acetate. The decanted aqueous phase was re-extracted with 50 ml of ethyl acetate and the combined organic phases were dried, filtered, rinsed and evaporated to dryness under reduced pressure. The residue was chromatographed over 200 g of silica gel and eluted with methylene chloride with 25% of ethyl acetate. The rich fractions were recovered and evaporated to dryness. The residue was dissolved in ether, and the solution was rinsed and dried to obtain 5.4 g of cis 3-phthalimido-4-chloromethyl-2-azetidinone.

Workup

  1. temperaturewas then cooled to room temperature
  2. customwas evaporated to dryness under reduced pressure
  3. addition250 ml of water and 150 ml of ethyl acetate were added to the residue
  4. additionsodium bicarbonate was added in small quantities until evolution of gas
  5. filtrationThe mixture was filtered
  6. washthe filtrate was rinsed with ethyl acetate
  7. extractionThe decanted aqueous phase was re-extracted with 50 ml of ethyl acetate
  8. customthe combined organic phases were dried
  9. filtrationfiltered
  10. washrinsed
  11. customevaporated to dryness under reduced pressure
  12. customThe residue was chromatographed over 200 g of silica gel
  13. washeluted with methylene chloride with 25% of ethyl acetate
  14. customThe rich fractions were recovered
  15. customevaporated to dryness
  16. dissolutionThe residue was dissolved in ether
  17. washthe solution was rinsed
  18. customdried

Sources & evidence

ORD record
ord-c9ba4ef8630644bdb86e1dac09f76f6a
Source dataset
uspto-grants-1991_10
Patent number
US05057512

Reaction notes

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