HCID 86739940, compound → HCID 86739941, compound

HRID 615858Notes

Reaction equation

HRID 615858 reaction equation
[N:1]([C@H:4]1[C@@H:7]([CH2:8][O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[N:6](C2C=CC(OC)=CC=2)[C:5]1=[O:23])=[N+:2]=[N-:3]>C(#N)C.O>[N:1]([C@H:4]1[C@@H:7]([CH2:8][O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[NH:6][C:5]1=[O:23])=[N+:2]=[N-:3]

Participants

4

Reactant 1

HCID 86739940HCID 86739940, compound

Product 1

HCID 86739941HCID 86739941, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of (±)-(cis)-[(3-azido-1-(4-methoxyphenyl)-2-oxo-4-azetidinyl)methoxy]acetic acid, methyl ester (2.054 g, 6.44 mmole) in acetonitrile (40 ml) was cooled to -5° C. A solution of ceric ammonium nitrate (10.62 g, 19.32 mmole) in water (30 ml) was added rapidly over ca. forty-five seconds. The reaction was warmed to +10° C. over fifteen minutes, diluted with water (100 ml), and extracted with ethyl acetate (two 80 ml portions). Sodium chloride was added to the aqueous layer which was again extracted with ethyl acetate (ca. 150 ml). The organic extracts were washed with saturated potassium bicarbonate, saturated sodium sulfite solution, brine, and dried (sodium sulfate). Filtration followed by solvent removal yielded 1.56 g of crude product which was chromatographed on silica gel (55 g, 230-400 mesh). Elution with 70% ethyl acetate-hexane yielded 1.1 g of the title compound as a heavy oil.

Workup

  1. temperatureThe reaction was warmed to +10° C. over fifteen minutes
  2. extractionextracted with ethyl acetate (two 80 ml portions)
  3. additionSodium chloride was added to the aqueous layer which
  4. extractionwas again extracted with ethyl acetate (ca. 150 ml)
  5. washThe organic extracts were washed with saturated potassium bicarbonate, saturated sodium sulfite solution, brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationFiltration
  8. customfollowed by solvent removal
  9. customyielded 1.56 g of crude product which
  10. customwas chromatographed on silica gel (55 g, 230-400 mesh)
  11. washElution with 70% ethyl acetate-hexane

Sources & evidence

ORD record
ord-4d3d588d0a6341ce93f6bb42506f32b1
Source dataset
uspto-grants-1985_02
Patent number
US04501697

Reaction notes

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