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HCID 12804816, Verbindung → HCID 12805476, Verbindung

HRID 258426
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 258426
S1C2C=CC=CC=2N=C1S[S:11][C@H:12]1[N:15]([CH:16]([C:33]([CH3:35])=[CH2:34])[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:36])[C@H:13]1[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O.[C:49]1([CH3:58])[CH:54]=[CH:53][C:52]([S:55]([O-:57])=[O:56])=[CH:51][CH:50]=1.[Na+]>CC(C)=O.O.[N+]([O-])([O-])=O.[Ag+]>[C:49]1([CH3:58])[CH:54]=[CH:53][C:52]([S:55]([S:11][C@H:12]2[N:15]([CH:16]([C:33]([CH3:35])=[CH2:34])[C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[C:14](=[O:36])[C@H:13]2[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)(=[O:57])=[O:56])=[CH:51][CH:50]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 12804816HCID 12804816, VerbindungHCID 23682957Sodium 4-methylbenzene-1-sulfinate hydrate

Produkt 1

HCID 12805476HCID 12805476, VerbindungAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24470Silver NitrateKatalysatorHCID 180AcetoneLösungsmittel3×
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of diphenylmethyl 2-[(3R,4R)-4-[(benzothiazol-2-yl)dithio]-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methyl-3-butenoate (XIIIa. 12.12 g, 0.0182 mole) in acetone (325 mL) and water (37 mL), silver nitrate (3.86 g, 0.0227 mole) was added all at once. A freshly prepared solution of sodium p-toluenesulfinate hydrate (4.05 g; 0.0227 mole) in acetone (255 mL) and water (37 mL) was added dropwise over 1 h, while the reaction mixture was protected from light. After an additional 1h period at room temperature, Celite (5 g) was added and the mixture was diluted with acetone (500 mL) and then was filtered. The filtrate was evaporated to a small volume, and the crude product was extracted into ether (3×250 mL). The ether phase was dried with magnesium sulfate and concentrated to afford a crude product. Flash chromatography (SiO2, eluting with 40% ethyl acetate in hexane) gave 9.05 g (73.5%) of the title compound as a white solid.

Aufarbeitung

  1. filtrationwas filtered
  2. customThe filtrate was evaporated to a small volume
  3. extractionthe crude product was extracted into ether (3×250 mL)
  4. dry with materialThe ether phase was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customto afford a crude product
  7. washFlash chromatography (SiO2, eluting with 40% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8d4c6a772b084f35beba24f23dfdd98d
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05266691

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