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

HRID 1461490Notes

Reaction equation

HRID 1461490 reaction equation
[Si:1]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[N:13](C(C(OCC)=O)=O)[C@@H:12]1[C@@H:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C>CO>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[NH:13][C@@H:12]1[C@@H:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25])[CH3:10])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86745314methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-1-(ethoxalyl)-4-oxoazetidin-2-yl]propionate

Product 1

HCID 11834034methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionateYield 68.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-1-(ethoxalyl)-4-oxoazetidin-2-yl]propionate (27 mg) in methanol (1 ml) was added triethylamine (27 μl) at room temperature. After stirring for 30 minutes, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine (twice) and water, dried over magnesium sulfate and evaporated to give methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate (14 mg).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine (twice) and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-2ce7b2b801e34f6fa3cb8a6b39071b39
Source dataset
uspto-grants-1991_12
Patent number
US05075437

Reaction notes

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