Water → HCID 13515986, compound

HRID 2118783Notes

Reaction equation

HRID 2118783 reaction equation
[C:1]([CH:6]1[N:9](C2C=CC(OC)=CC=2)[C:8](=[O:18])[CH:7]1[O:19][CH3:20])([O:3][CH2:4][CH3:5])=[O:2].[N+]([O-])([O-])=O.[NH4+].O.S([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[C:1]([CH:6]1[NH:9][C:8](=[O:18])[CH:7]1[O:19][CH3:20])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 22985Ammonium nitrateHCID 24437Sodium SulfiteHCID 13922272HCID 13922272, compound

Product 1

HCID 13515986HCID 13515986, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.4 g of 4-carboethoxy-3-methoxy-1-(p-methoxyphenyl)azetidin-2-one in 50 ml acetonitrile at 0° was added a solution of 8.23 g of cerric ammonium nitrate in 50 H2O over 3 minutes. After stirring at 0° for 1 hour the solution was poured into 200 ml of 10% sodium sulfite and extracted with 3×75 ml of ethyl acetate. The combined organic extracts were washed with 10% sodium sulfite and saturated sodium chloride solutions and dried over sodium sulfate. Filtration and evaporation gave an amber oil which was recrystallized from methylene chloride/hexane to give 700 mg of 4-carboethoxy-3-methoxyazetidine-2-one; m.p. 91°-92°.

Workup

  1. extractionextracted with 3×75 ml of ethyl acetate
  2. washThe combined organic extracts were washed with 10% sodium sulfite and saturated sodium chloride solutions
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and evaporation
  5. customgave an amber oil which
  6. customwas recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-fad4130df724427b9be43edcdd745c11
Source dataset
uspto-grants-1987_07
Patent number
US04680391

Reaction notes

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