Water → HCID 54485418, compound

HRID 1603652Notes

Reaction equation

HRID 1603652 reaction equation
O=O.[C:3]([S:6][C@H:7]1[N:10]([C:11](=C(C)C)[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:13])[C:9](=[O:27])[C@@H:8]1[Br:28])(=[O:5])[CH3:4].P(OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(OCC)(=O)C>[C:3]([S:6][C@H:7]1[N:10]([CH2:11][C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[O:13])[C:9](=[O:27])[C@@H:8]1[Br:28])(=[O:5])[CH3:4]

Participants

7

Reactant 5

HCID 962WaterHCID 977OxygenHCID 6101p-Toluenesulfonic acidHCID 8472Trimethyl phosphiteHCID 10072027HCID 10072027, compound

Product 1

HCID 54485418HCID 54485418, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ozonised oxygen was bubbled through a solution of p-methoxybenzyl 2[(3S, 4R)-4-acetylthio-3-bromo-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (Osborne N. F. et al., J. Chem. Soc. Perkin Trans. 1, 1994, 179) (20.16 g, 0.0456 mol) in ethyl acetate (400 ml) at -65° to -70° C. until a permanent blue solution was obtained. Excess ozone was removed by the passage of oxygen, then trimethyl phosphite (53.8 ml, 0.456 mol) was added dropwise. After 15 min. the solution was allowed to warm to room temperature, then stood for 16 hr. The solvents were evaporated and the residue reevaporated twice from toluene, then dissolved in ethyl acetate (300 ml) and stirred vigorously for 1.5 hr. with a solution of p-toluenesulphonic acid (2 g) in water (100 mol). After dilution with water the organic layer was separated and the aqueous layer further extracted with ethyl acetate. The combined extracts were washed successively with saturated aq. sodium hydrogen carbonate and brine, then dried ((MgSO4) and evaporated. Purification by flash chromatography (silica, ethyl acetate-pet. ether) gave the product as a light brown oil, yield 10.6 g (58%).

Workup

  1. customwas obtained
  2. customExcess ozone was removed by the passage of oxygen
  3. waitstood for 16 hr
  4. customThe solvents were evaporated
  5. customthe residue reevaporated twice from toluene
  6. dissolutiondissolved in ethyl acetate (300 ml)
  7. customAfter dilution with water the organic layer was separated
  8. extractionthe aqueous layer further extracted with ethyl acetate
  9. washThe combined extracts were washed successively with saturated aq. sodium hydrogen carbonate and brine
  10. dry with materialdried ((MgSO4)
  11. customevaporated
  12. customPurification by flash chromatography (silica, ethyl acetate-pet. ether)

Sources & evidence

ORD record
ord-496ce3888a1f42bf8dcc67b1d126357d
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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