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

HRID 231227

반응식

HRID 231227 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24544Mercuric sulfate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc66650d54a44bf4858200e34e1686f6
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845210

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