تفاعل #1338181

معادلة التفاعل

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

المردود 89.0%

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

المردود 89.0%

المذيبات

methanol water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   أخرىwas continued until the full consumption of the starting material
3. 3
   أخرىAfter the completion of the reaction
4. 4
   workup.ADDITIONwas added to the reaction mixture
5. 5
   غسيلAfter washing with methylene chloride (5 ml)
6. 6
   أخرىThe crystals so precipitated
7. 7
   ترشيحwere collected by filtration
8. 8
   غسيلwashed with water
9. 9
   أخرىdried

الإجراء التجريبي

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%).

المصدر