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

HRID 1250999Notes

Reaction equation

HRID 1250999 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:31])[C:16](N2[C@H]3C4C=CC=CC=4C[C@H]3OC2=O)=[O:17])[NH:13][C:12]1=[O:32])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH2:33].OO.[OH-].[Na+].O>CO.O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:31])[C:16]([OH:17])=[O:33])[NH:13][C:12]1=[O:32])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 449047Hydrogen peroxide waterHCID 1317231003-{(2R)-2-[(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl)propionyl}-(3aS-cis)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one

Product 1

HCID 9882831(R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acidYield 89%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 3-{(2R)-2-[(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl)propionyl}-(3aS-cis)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one (308 mg) dissolved in a methanol-water solvent mixture (2:1, 3 ml), 30% hydrogen peroxide water (0.15 g, 1.35 mmol) was added at room temperature. To the resulting mixture, a 28% aqueous solution of sodium hydroxide (0.12 g, 0.81 mmol) was added dropwise at the same temperature. Stirring was continued until the full consumption of the starting material was confirmed by HPLC. After the completion of the reaction, cool water (10 ml) was added to the reaction mixture. After washing with methylene chloride (5 ml), the pH of the mixture was adjusted to 2 with 35% hydrochloric acid. The crystals so precipitated were collected by filtration, washed with water and then dried, whereby 160 mg (β:α=96:4) of the colorless title compound was obtained (yield: 89%).

Workup

  1. additionwas added at room temperature
  2. customwas continued until the full consumption of the starting material
  3. customAfter the completion of the reaction
  4. additionwas added to the reaction mixture
  5. washAfter washing with methylene chloride (5 ml)
  6. customThe crystals so precipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-f3f577e36d16429eb93ec3bea32b6006
Source dataset
uspto-grants-2002_01
Patent number
US06340751B1

Reaction notes

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