Oxygen → HCID 54192423, compound

HRID 1603673Notes

Reaction equation

HRID 1603673 reaction equation
O=O.[C:3]([S:6][C@H:7]1[N:10]([C:11](=C(C)C)[C:12]([O:14][CH3:15])=[O:13])[C:9](=[O:19])[C@@H:8]1[Cl:20])(=[O:5])[CH3:4].P(OC)(OC)OC>C(OCC)(=O)C>[C:3]([S:6][C@H:7]1[N:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:9](=[O:19])[C@@H:8]1[Cl:20])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 977OxygenHCID 8472Trimethyl phosphiteHCID 86754830HCID 86754830, compound

Product 1

HCID 54192423HCID 54192423, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ozonised oxygen was bubbled through a solution of methyl 2-[(3S,4R)-4-acetylthio-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (7.6 g, 0.026 mol) in ethyl acetate (300 ml) at -65 to -70° C. until a permanent blue colour was obtained. Excess ozone was removed by the passage of oxygen, then trimethyl phosphite (30.7 ml, 0.26 mol) was added dropwise. After 15 minutes the solution was allowed to warm to room temperature and stirred for 19 hr. The solvents were evaporated and the residue reevaporated twice from toluene, then disolved in ethyl acetate (175 ml) and stirred vigourously with a solution of p-toluenesulphonic acid (1.14 g) in water (60 ml). After dilution with water the organic layer was separated and the aqueous layer further extracted with ethyl acetate. The combined organic extracts were washed successively with saturated aq. sodium hydrogen carbonate and brine, dried (MgSO4) and evaporated. Purification by flash chromatography (silica, pet. ether-ethyl acetate) gave the title compound as a colourless solid 3.69 g (56%, m.p. 82-83° C.).

Workup

  1. customwas obtained
  2. customExcess ozone was removed by the passage of oxygen
  3. customThe solvents were evaporated
  4. customthe residue reevaporated twice from toluene
  5. stirringstirred vigourously with a solution of p-toluenesulphonic acid (1.14 g) in water (60 ml)
  6. customAfter dilution with water the organic layer was separated
  7. extractionthe aqueous layer further extracted with ethyl acetate
  8. washThe combined organic extracts were washed successively with saturated aq. sodium hydrogen carbonate and brine
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customPurification by flash chromatography (silica, pet. ether-ethyl acetate)

Sources & evidence

ORD record
ord-55d7433909a241dc8ff4acb8cf933b02
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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