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

HRID 482129ノート

反応式

HRID 482129 の反応式
[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]

参加物

6

反応物 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)

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad15dc65a3a54a3eaefb954bbc725201
出典データセット
uspto-grants-1998_08
特許番号
US05792861

反応ノート

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