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

HRID 1250998Notes

Reaction equation

HRID 1250998 reaction equation
[O:1]1CCCC1.[Si:6]([O:13][C@@H:14]([C@@H:16]1[C@@H:19]([C@@H:20]([CH3:40])[C:21](C2C=C(C)C=CC=2S(NC2CCCCC2)(=O)=O)=[O:22])[NH:18][C:17]1=[O:41])[CH3:15])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH-].[Na+]>O>[Si:6]([O:13][C@@H:14]([C@@H:16]1[C@@H:19]([C@@H:20]([CH3:40])[C:21]([OH:22])=[O:1])[NH:18][C:17]1=[O:41])[CH3:15])([C:9]([CH3:10])([CH3:11])[CH3:12])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 699481593-{(2R)-2-[(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-N-cyclohexyl-p-toluenesulfonamide

Product 1

HCID 9882831(R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acidYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran solution (2:1, 3.5 ml) of 3-{(2R)-2-[(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-N-cyclohexyl-p-toluenesulfonamide (218 mg, 0.4 mmol, β:α=88:12), 0.5N aqueous sodium hydroxide (1.8 ml) was added dropwise at room temperature, followed by stirring for 3 hours at the same temperature. To the reaction mixture, 5 ml of water was then poured and the resulting mixture was washed with methylene chloride. The aqueous layer was acidified to pH 2 with 2N-hydrochloric acid. The crystals so precipitated were collected by filtration, washed with water, and then dried under reduced pressure, whereby 84 mg (β:α=89:11) of the colorless title compound was obtained (yield: 69%).

Workup

  1. washthe resulting mixture was washed with methylene chloride
  2. customThe crystals so precipitated
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. dry with materialdried under reduced pressure, whereby 84 mg (β:α=89:11) of the colorless title compound
  6. customwas obtained (yield: 69%)

Sources & evidence

ORD record
ord-fa2d71596bca4bbe9866ba64597d5054
Source dataset
uspto-grants-2002_01
Patent number
US06340751B1

Reaction notes

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