反应 #1338181

反应方程式

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

hydrogen peroxide water

sodium hydroxide

water

→

title compound

收率 89.0%

(R)-2-[(3S,4S)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionic acid

收率 89.0%

溶剂

methanol water

反应条件

后处理

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   其他was continued until the full consumption of the starting material
3. 3
   其他After the completion of the reaction
4. 4
   workup.ADDITIONwas added to the reaction mixture
5. 5
   洗涤After washing with methylene chloride (5 ml)
6. 6
   其他The crystals so precipitated
7. 7
   过滤were collected by filtration
8. 8
   洗涤washed with water
9. 9
   其他dried

实验过程

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%).

来源