Sulfuric Acid → cis-4-Acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

HRID 231227

反応式

HRID 231227 の反応式
[Si:1]([O:8][C@@H:9]([C@H:11]1[C@@H:14]([C:15]#[C:16][Si](C)(C)C)[NH:13][C:12]1=[O:21])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:23].C(=O)([O-])O.[Na+].C(OCC)(=O)C.O>O1CCCC1.O.S([O-])([O-])(=O)=O.[Hg+2]>[C:15]([C@H:14]1[NH:13][C:12](=[O:21])[C@H:11]1[CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:10])(=[O:23])[CH3:16]

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22728543Water ethylacetateHCID 57192380Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone

生成物 1

HCID 67789429cis-4-Acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone収率 18.1%

試薬・触媒・溶媒 3

HCID 24544Mercuric sulfate触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone (0.24 g) is dissolved in a mixture of tetrahydrofuran (5 ml) and water (1 ml), and mercury sulfate (0.03 g) and concentrated sulfuric acid (0.06 g) are added, followed by stirring at room temperature for 15 hours. After addition of sodium hydrogen carbonate (0.2 g), the reaction mixture is poured into ethyl acetate-water, and the organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography to give 0.03 g of cis-4-acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone.

後処理

  1. additionare added
  2. customthe organic layer is separated
  3. washwashed with aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cc66650d54a44bf4858200e34e1686f6
出典データセット
uspto-grants-1989_07
特許番号
US04845210

関連ノート

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