Acetic Acid → (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid

HRID 1461488Notes

Reaction equation

HRID 1461488 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)[NH:13][C:12]1=[O:23])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:25].[Na+].C(O)(=O)C>O1CCCC1>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:12](=[O:23])[NH:13][C@@H:14]1[C@@H:15]([CH3:22])[C:16]([OH:21])=[O:25])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23667635Sodium periodateHCID 57230061(3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1R)-3-hydroxy-1,3-dimethyl-2-oxobutyl]-2-azetidinone

Product 1

HCID 9882831(R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1R)-3-hydroxy-1,3-dimethyl-2-oxobutyl]-2-azetidinone (135 mg) in tetrahydrofuran (4 ml) was added 1M solution of sodium periodate buffered with acetic acid (mole ratio 1:1) (7.8 ml) at room temperature and the mixture was stirred for 1 day at the same temperature. The reaction mixture was evaporated, acidified, and extracted twice with dichloromethane. The organic layer was washed twice with brine, dried over magnesium sulfate and evaporated to give (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (85 mg).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted twice with dichloromethane
  3. washThe organic layer was washed twice with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f8a7f1efbcd84dcd8b27313c6446b28b
Source dataset
uspto-grants-1991_12
Patent number
US05075437

Reaction notes

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