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

HRID 482129노트

반응식

HRID 482129 반응식
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:31])[C:16](N2C(=O)C3C=CC=CC=3OC2(C)C)=[O:17])[NH:13][C:12]1=[O:32])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[OH:34].O.OO.[OH-].[Na+]>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:34])[NH:13][C:12]1=[O:32])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 100044493-[(R)-2-[(3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl]-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-oneHCID 22242641Methanol--water (1/1)

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 3-[(R)-2-[(3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl]-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one (7.0 g, 15 mmol) in a solvent mixture of methanol/water (2:1, 45 ml), a 30% aqueous solution of hydrogen peroxide (3.5 g, 30 mmol) was added at room temperature. Then a 28% aqueous solution of sodium hydroxide (2.4 g, 17 mmol) was added dropwise into it and the obtained mixture was stirred until the starting material disappeared in HPLC. After the completion of the reaction, 45 ml of cold water was added to the reaction mixture. After washing with 15 ml of methylene chloride, 35% hydrochloric acid was added to thereby adjust the pH value of the mixture to 3. The crystals thus precipitated were collected by filtration, washed with water and dried. Thus 4.3 g of (R)-2-[(3S,4S)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionic acid was obtained.

후처리

  1. additionwas added to the reaction mixture
  2. washAfter washing with 15 ml of methylene chloride, 35% hydrochloric acid
  3. additionwas added
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-ad15dc65a3a54a3eaefb954bbc725201
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792861

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