Dimethyl Sulfide → (3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone

HRID 231240

反応式

HRID 231240 の反応式
ClC1C=CC=[C:4]([C:8](OO)=[O:9])C=1.C([C@H:15]1[NH:18][C:17](=[O:19])[C@H:16]1[C@H:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH3:21])(=O)C.C(=O)([O-])[OH:31].[Na+].CSC>C(OCC)(=O)C>[C:8]([O:19][C@H:17]1[NH:18][C:15](=[O:31])[C@H:16]1[C@H:20]([O:22][Si:23]([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25])[CH3:21])(=[O:9])[CH3:4]

参加物

6

実験手順

m-Chloroperbenzoic acid (0.5 g) is added to a solution of the object compound of Example 22 (0.08g) in ethyl acetate (8 ml), and the mixture is stirred at room temperature for 3 days and then poured into a mixture of ethyl acetate (50 ml), aqueous sodium hydrogen carbonate (20 ml) and dimethyl sulfide (0.4 ml). The mixture is stirred at room temperature for 30 minutes. The organic layer is separated, washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography (eluent: 15% ethyl acetate-85% hexane) to give 0.045 g of (3S,4R)-4-acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone.

後処理

  1. stirringThe mixture is stirred at room temperature for 30 minutes
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-295a58d7d27a4aad9f5d6f9e24a55e1f
出典データセット
uspto-grants-1989_07
特許番号
US04845210

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