benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate → Benzhydryl (E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)-vinyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 263747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263747
[CH:1]([C@:3]1([CH3:27])[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=O.[Cl-].[O:29]1[CH:33]=[N:32][C:31]([CH2:34][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:30]1>C1OC1CC>[CH3:27][C@@:3]1(/[CH:1]=[CH:34]/[C:31]2[N:32]=[CH:33][O:29][N:30]=2)[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:12]

Komponenten

4

Edukt 2

HCID 10762402benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateHCID 19038908(1,2,4-Oxadiazol-3-yl)methyl-triphenylphosphonium chloride

Produkt 1

HCID 86750939Benzhydryl (E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)-vinyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 78341,2-EpoxybutaneLösungsmittel

Versuchsvorschrift

1.14 g (3.0 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 15 ml of 1,2-butylene oxide, treated with 1.38 g (3.6 mmol) of (1,2,4-oxadiazol-3-yl)methyl-triphenylphosphonium chloride and refluxed for 10 hours. Subsequently, the mixture was filtered, the filtrate is evaporated and the residual brown oil was chromatographed over silica gel (0.040-0.063 mm particle size) with methylene chloride as the eluent. Yield: 280 mg (21%) of colorless crystals MS: (M+NH4)+ 465.3 IR (KBr): 1792, 1753, 1658, 1492, 1200, 991 cm-1

Aufarbeitung

  1. temperaturerefluxed for 10 hours
  2. filtrationSubsequently, the mixture was filtered
  3. customthe filtrate is evaporated
  4. customthe residual brown oil was chromatographed over silica gel (0.040-0.063 mm particle size) with methylene chloride as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-e092ac7f19b34dfca418ad654158364b
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05644053

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