Oxalic acid dihydrate → (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1R)-3-hydroxy-1,3-dimethyl-2-oxobutyl]-2-azetidinone

HRID 1461487Notes

Reaction equation

HRID 1461487 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:26])[C:16](=[O:25])[C:17]([CH3:24])([O:19][Si](C)(C)C)[CH3:18])[NH:13][C:12]1=[O:27])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.O.C(O)(=O)C(O)=O>CO>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:26])[C:16](=[O:25])[C:17]([OH:19])([CH3:24])[CH3:18])[NH:13][C:12]1=[O:27])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 57183497(3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1R)-1,3-dimethyl-3-(trimethylsilyloxy)-2-oxobutyl]-2-azetidinone

Product 1

HCID 57230061(3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1R)-3-hydroxy-1,3-dimethyl-2-oxobutyl]-2-azetidinoneYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1R)-1,3-dimethyl-3-(trimethylsilyloxy)-2-oxobutyl]-2-azetidinone (132 mg) in methanol (6 ml) was added oxalic acid dihydrate (200 mg) at room temperature and the mixture was stirred for 1 hour. The reaction mixture was evaporated, and diethyl ether (30 ml) and saturated aqueous sodium bicarbonate (10 ml) were slowly added to the residue. The solution was extracted twice with diethyl ether, and the extracts were combined and washed in turn with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate and evaporated to give (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1R)-3-hydroxy-1,3-dimethyl-2-oxobutyl]-2-azetidinone (109 mg).

Workup

  1. customThe reaction mixture was evaporated
  2. additiondiethyl ether (30 ml) and saturated aqueous sodium bicarbonate (10 ml) were slowly added to the residue
  3. extractionThe solution was extracted twice with diethyl ether
  4. washwashed in turn with saturated aqueous sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-6bf6756e71404d57893c3f8fcce4b3d6
Source dataset
uspto-grants-1991_12
Patent number
US05075437

Reaction notes

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