HCID 86739939, compound → HCID 86740203, compound

HRID 867663Notes

Reaction equation

HRID 867663 reaction equation
[N:1]([C@H:4]1[C@@H:7]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6](C2C=CC(OC)=CC=2)[C:5]1=[O:24])=[N+:2]=[N-:3]>O.C(#N)C>[N:1]([C@H:4]1[C@@H:7]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:6][C:5]1=[O:24])=[N+:2]=[N-:3]

Participants

4

Reactant 1

HCID 86739939HCID 86739939, compound

Product 1

HCID 86740203HCID 86740203, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10.22 g of ceric ammonium nitrate in 13 ml of water at 0° C. is added 1.99 g of (±)-(cis)-3-azido-1-(4-methoxyphenyl)-2-oxo-4-(2-phenylethenyl)azetidine dissolved in 65 ml of acetonitrile during a 15 minute period (additional 10 ml of acetonitrile is used for rinse). The mixture is stirred for an additional 15 minutes at 0° C., diluted with 750 ml of ethyl acetate, washed with water (six 600 ml portions), dried over anhydrous sodium sulfate, and stripped of solvent to give an oil. The crude product is chromatographed on 90 g of silica gel, eluting first with 250 ml of 30% ethyl acetate/petroleum ether, then 50% ethyl acetate/petroleum ether. Fractions (50 ml each) 11-16 are combined and evaporated to give 802 mg of the title compound as an oil.

Workup

  1. wash(additional 10 ml of acetonitrile is used for rinse)
  2. additiondiluted with 750 ml of ethyl acetate
  3. washwashed with water (six 600 ml portions)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customto give an oil
  6. customThe crude product is chromatographed on 90 g of silica gel
  7. washeluting first with 250 ml of 30% ethyl acetate/petroleum ether
  8. customevaporated

Sources & evidence

ORD record
ord-b1deb62605c04a4c850d26aab32e0d4b
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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