Metaperiodic acid → HCID 53656896, compound

HRID 1377453Notes

Reaction equation

HRID 1377453 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[NH:25][C:26](=[O:34])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)CO1>O1CCCC1.O>[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[NH:25][C:26](=[O:34])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:11]

Participants

5

Reactant 2

HCID 65185Metaperiodic acidHCID 57295923HCID 57295923, compound

Product 1

HCID 53656896HCID 53656896, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Periodic acid (18.7 g, 45.6mmol) was added to a suspension of (3S,4S)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-3-phenylacetamidoazetidin-2-one (15.1 g, 36.8mmol) in tetrahydrofuran (210 ml) and water (210 ml). The reaction mixture was heated under reflux for 1.5 h and then cooled in ice. The precipitated product was collected by filtration, washed with water and dried over phosphorus pentoxide to yield the title compound as a mixture of aldehyde and the corresponding hydrate (10.18 g, 82%); νmax (KBr) 1713, 1638, 1552 and 1514cm-1 ; aldehyde δH (d6 -DMSO) 3.43 and 3.50 (2H, ABq, J 14.4 Hz), 3.73 (3H, s), 4.95 (1H, dd, J 6.1, 1.2 Hz), 5.19 (1H, m), 6.95 (2H, d, J 9.0 Hz), 7.18-7.35 (7H, m), 9.09 (1H, d, J 7.3 Hz) and 9.52 (1H, d, J 1.2 Hz); hydrate δH (d6 -DMSO) 3.50 (2H, s), 3.72 (3H, s), 4.16 (1H, t, J 5.6 Hz), 5.07 (1H, q, J 5.8 Hz), 5.29 (1H, dd, J 9.4, 5.6 Hz), 6.28 (2H, t, J 6.7 Hz, exch.), 6.9 (2H, d, J 9.1 Hz), 7.19-7.35 (5H, m), 7.52 (2H, J 9.1 Hz) and 8.52 (1H, d, J 9.4 Hz); m/z (EI) 338 (10); (CI, +ve ion, ammonia) 339 (MH+), 356 (MNH3+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1.5 h
  3. temperaturecooled in ice
  4. filtrationThe precipitated product was collected by filtration
  5. washwashed with water
  6. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-080e909f54b443dfb2f8445c843c78ae
Source dataset
uspto-grants-1997_09
Patent number
US05665717

Reaction notes

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