Metaperiodic acid → HCID 15675162, compound

HRID 861894Notes

Reaction equation

HRID 861894 reaction equation
I(O)(=O)(=O)=O.CC1(C)[O:11][C@H:10]([C@H:12]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:14](=[O:24])[C@H:13]2[N:25]2[C:29](=[O:30])[C:28]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]3[C:26]2=[O:35])CO1>C1COCC1>[CH:10]([C@H:12]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:14](=[O:24])[C@H:13]1[N:25]1[C:26](=[O:35])[C:27]2=[CH:34][CH:33]=[CH:32][CH:31]=[C:28]2[C:29]1=[O:30])=[O:11]

Participants

4

Reactant 2

HCID 65185Metaperiodic acidHCID 57221965HCID 57221965, compound

Product 1

HCID 15675162HCID 15675162, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 50% w/w periodic acid (6.3 ml, 22 mmol) was added to (3S,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-3-phthalimido-azetidin-2-one (4.22 g, 10 mmol) in 50% aqueous THF (75 ml) and heated under reflux for 2.5h. The cooled solution was extracted twice with ethyl acetate and the combined extracts washed twice with water then with brine, dried and evaporated to give a colourless solid. The solid was triturated with ether and the title compound filtered off and dried in vacuo (3.151 g, 90%); [α]D -214.3° (c=1.00 CHCl3); νmax (CHCl3) 1785 (sh), 1769, 1727, 1514, 1391, 1250, and 1124 cm-1 ; δH (CDCl3) 3.73 (3H, s), 4.77 (1H, dd, J 6.29, 2.78 Hz), 5.80 (1 H, d, J 5.80 Hz), 6.95 and 7.39 (4H, ABq, J 8.97 Hz), 7.7-8.0 (4H, m) and 9.90 (1H, d, J 2.73 Hz); m/z (EI) 350 (14), 149 (100%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5h
  3. extractionThe cooled solution was extracted twice with ethyl acetate
  4. washthe combined extracts washed twice with water
  5. dry with materialwith brine, dried
  6. customevaporated
  7. customto give a colourless solid
  8. customThe solid was triturated with ether
  9. filtrationthe title compound filtered off
  10. customdried in vacuo (3.151 g, 90%)

Sources & evidence

ORD record
ord-a82ccebdf65e4a0f9dd8500495471147
Source dataset
uspto-grants-1998_02
Patent number
US05716948

Reaction notes

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