Metaperiodic acid → HCID 67867010, compound

HRID 1461489Notes

Reaction equation

HRID 1461489 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:22])[C:16](=[O:21])C(O)(C)C)[N:13]([C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:24])[C:12]1=[O:30])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I(O)(=O)(=O)=[O:32]>CO>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:12](=[O:30])[N:13]([C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:24])[C@@H:14]1[C@@H:15]([CH3:22])[C:16]([OH:32])=[O:21])[CH3:10])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 65185Metaperiodic acidHCID 67867163HCID 67867163, compound

Product 1

HCID 67867010HCID 67867010, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(ethoxalyl)-4-[(1R)-3-hydroxy-1,3-dimethyl-2-oxobutyl]-2-azetidinone (50 mg) in methanol (2 ml) was added 0.54M aqueous periodic acid solution (1.0 ml). After stirring at room temperature for 5 hours, the solvent was removed in vacuo and the residue was extracted with dichloromethane. The extract was dried over magnesium sulfate and evaporated to afford (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-1-(ethoxalyl)-4-oxoazetidin-2-yl]propionic acid (93 mg). To a solution of the compound obtained above in diethyl ether (2 ml) was added a solution of diazomethane in diethyl ether at room temperature. The solvent was removed in vacuo and the residue was chromatographed on silica gel (1 g) eluting with a mixture of ethyl acetate and hexane (1:5, V/V) to give methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-1-(ethoxalyl)-4-oxoazetidin-2-yl]propionate (24 mg).

Workup

  1. customthe solvent was removed in vacuo
  2. extractionthe residue was extracted with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-4fb6d8e072e042f4b37b46253154cf33
Source dataset
uspto-grants-1991_12
Patent number
US05075437

Reaction notes

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