Hydrochloric Acid → methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate

HRID 1461486Notes

Reaction equation

HRID 1461486 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH:15](C)[C:16](=O)N2CCSC2=S)[NH:13][C:12]1=[O:25])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:26](=[O:29])([O-])[O-:27].[K+].[K+].[Cl-].[Na+].Cl.[CH3:35]O>C(OCC)(=O)C>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:12](=[O:25])[NH:13][C@@H:14]1[C@@H:15]([CH3:16])[C:26]([O:27][CH3:35])=[O:29])[CH3:10])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 57016647(3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1RS)-1-methyl-2-oxo-2-(2-thioxothiazolidin-3-yl)ethyl]-2-azetidinone

Product 1

HCID 11834034methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(1RS)-1-methyl-2-oxo-2-(2-thioxothiazolidin-3-yl)ethyl]-2-azetidinone obtained in Example 2 (797 mg) in methanol (16 ml) was added potassium carbonate (410 mg) at 0° C. and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was poured into a mixture of ethyl acetate (40 ml), saturated aqueous sodium chloride (25 ml) and 1N hydrochloric acid (3 ml). The organic layer was separated, washed with saturated aqueous sodium chloride solution (30 ml ×2), dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (21 g) eluting with a mixture of hexane and ethyl acetate (3:2, V/V) to give methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate (597 mg) containing a very small amount of methyl (2S)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride solution (30 ml ×2)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (21 g)
  6. washeluting with a mixture of hexane and ethyl acetate (3:2, V/V)

Sources & evidence

ORD record
ord-0b1d0ca985424a36a6b9b5ef0c3ea542
Source dataset
uspto-grants-1991_12
Patent number
US05075437

Reaction notes

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