Allyl dihydroxyacetate → (3S,4S)-1-[(1R)-1-(allyloxycarbonyl)-1-hydroxymethyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

HRID 1464725

Reaktionsgleichung

Reaktionsgleichung von HRID 1464725
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@@H:7]([C@@H:9]1[C@@H:12]([C@H:13]([C:15]([S:17][CH3:18])=[S:16])[CH3:14])[NH:11][C:10]1=[O:19])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH:22][CH:23](O)[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25]>C1(C)C=CC=CC=1>[CH2:27]([O:26][C:24]([C@H:23]([N:11]1[C@H:12]([C@H:13]([C:15]([S:17][CH3:18])=[S:16])[CH3:14])[C@@H:9]([C@H:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:20])[CH3:21])[CH3:8])[C:10]1=[O:19])[OH:22])=[O:25])[CH:28]=[CH2:29]

Komponenten

4

Edukt 2

HCID 11105398Allyl dihydroxyacetateHCID 57309161(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-[(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

Produkt 1

HCID 86747780(3S,4S)-1-[(1R)-1-(allyloxycarbonyl)-1-hydroxymethyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidineAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (3S,4S)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine (700 mg) in toluene (7 ml) was added allyl dihydroxyacetate (560 mg), and the mixture was heated under reflux for 3 hours. The solution was washed with water, dried, and evaporated under reduced pressure to give a mixture (903 mg) of (3S,4S)-1-[(1R)-1-(allyloxycarbonyl)-1-hydroxymethyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine and (3S,4S)-1-[(1S)-1-(allyloxycarbonyl)-1-hydroxymethyl]-3[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washThe solution was washed with water
  4. customdried
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9430cc9ba8a84ed8933a46503d114ac3
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306816

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