Acetic Acid → allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464735
[Si]([O:8][C@@H:9]([C@H:11]1[C:17](=[O:18])[N:16]2[C@@H:12]1[C@@H:13]([CH3:27])[C:14]([S:25][CH3:26])=[C:15]2[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:17](=[O:18])[N:16]2[C@@H:12]1[C@@H:13]([CH3:27])[C:14]([S:25][CH3:26])=[C:15]2[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH3:10]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 57185440allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Produkt 1

HCID 57069192allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (100 mg) was added to a mixture of 70% aqueous tetrabutylammonium fluoride (0.71 g) and acetic acid (121 mg) in tetrahydrofuran (2 ml) and the mixture was allowed to stand at ambient temperature for 24 hours. The solution was diluted with ethyl acetate (6 ml), washed with water, aqueous sodium bicarbonate solution and brine, and dried. The solvent was removed off under reduced pressure and the residue was crystallized from n-hexane to afford allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (58.4 mg).

Aufarbeitung

  1. washwashed with water, aqueous sodium bicarbonate solution and brine
  2. customdried
  3. customThe solvent was removed off under reduced pressure
  4. customthe residue was crystallized from n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ad500ece2b014042ad68262e46bb326a
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306816

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