Dichloromethane → (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

HRID 1464726

Reaktionsgleichung

Reaktionsgleichung von HRID 1464726
ClCCl.[C:4]([Si:8]([CH3:24])([CH3:23])[O:9][C@@H:10]([C@@H:12]1[C@@H:15]([C@H:16]([C:18]([S:20][CH3:21])=[S:19])[CH3:17])[NH:14][C:13]1=[O:22])[CH3:11])([CH3:7])([CH3:6])[CH3:5].[Si](O[C@@H]([C@@H]1[C@@H]([C@@H](C(SC)=S)C)NC1=O)C)(C(C)(C)C)(C)C.Cl[C:47](=[O:54])[C:48]([O:50][CH2:51][CH:52]=[CH2:53])=[O:49]>C(N(CC)CC)C>[CH2:51]([O:50][C:48](=[O:49])[C:47]([N:14]1[C@H:15]([C@H:16]([C:18]([S:20][CH3:21])=[S:19])[CH3:17])[C@@H:12]([C@H:10]([O:9][Si:8]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:23])[CH3:24])[CH3:11])[C:13]1=[O:22])=[O:54])[CH:52]=[CH2:53]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 3018516Allyl chlorooxoacetateHCID 57193536(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidineHCID 57309161(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-[(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

Produkt 1

HCID 86747781(3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidineAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of dichloromethane (32.6 mg) and a mixture (33.1 mg) of (3S,4S)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine and (3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine were added triethylamine (30.4 mg) and allyl chloroglyoxylate (32.6 mg) successively at 0° C. After stirring for 10 minutes at the same temperature, the solution was washed with water, 1N hydrochloric acid, brine, and dried. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (5% diethyl ether-hexane) to afford a mixture (23 mg) of (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine and (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine.

Aufarbeitung

  1. washthe solution was washed with water, 1N hydrochloric acid, brine
  2. customdried
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography (5% diethyl ether-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4f04df132e48462c8d5931f18fe46f72
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306816

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