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Dimethyl Sulfoxide → (3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone

HRID 231237
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 231237
FC(F)(F)C(O)=O.CS(C)=O.[Si:12]([N:19]1[C@H:22]([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C@H:21]([C@H:29]([OH:31])[CH3:30])[C:20]1=[O:32])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl.O.C(OCC)(=O)C>[C:29]([C@@H:21]1[C@@H:22]([C:23]#[C:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[N:19]([Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:20]1=[O:32])(=[O:31])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 67788869cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone

Produkt 1

HCID 53923801(3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinoneAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

In an argon stream, a solution of dry trifluoroacetic acid (0.2 ml) in methylene chloride (3 ml) is added dropwise to a mixture of dimethyl sulfoxide (0.1 ml) and methylene chloride (10 ml) at -65° C. or lower, and the mixture is stirred at -70° C. for 0.5 hours. A solution of cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.4 g) in methylene chloride (4 ml) is added dropwise at -65° C. or lower and the mixture is stirred at the same temperature for 0.5 hour. After addition of triethylamine (0.3 ml) at the same temperature, the temperature is gradually raised to room temperature. The reaction mixture is poured into a mixture of ethyl acetate (70 ml) and water (100 ml), 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 (eluent: 3% ethyl acetate-97% n-hexane) to give trans i.e. (3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone (0.13 g)

Aufarbeitung

  1. stirringlower and the mixture is stirred at the same temperature for 0.5 hour
  2. temperaturethe temperature is gradually raised to room temperature
  3. customthe organic layer is separated
  4. washwashed with aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bbcc503110d94085a8f8865eb0323174
Quelldatensatz
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04845210

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