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HCID 12912424, Verbindung → HCID 54435877, Verbindung

HRID 258427
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 258427
S1C2C=CC=CC=2N=C1S[S:11][C@H:12]1[N:15]([CH:16]([C:30]([CH3:32])=[CH2:31])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:33])[C@H:13]1[NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O.[C:46]1([CH3:55])[CH:51]=[CH:50][C:49]([S:52]([O-:54])=[O:53])=[CH:48][CH:47]=1.[Na+]>CC(C)=O.O.[N+]([O-])([O-])=O.[Ag+]>[C:46]1([CH3:55])[CH:51]=[CH:50][C:49]([S:52]([S:11][C@H:12]2[N:15]([CH:16]([C:30]([CH3:32])=[CH2:31])[C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])[C:14](=[O:33])[C@H:13]2[NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)(=[O:54])=[O:53])=[CH:48][CH:47]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 12912424HCID 12912424, VerbindungHCID 23682957Sodium 4-methylbenzene-1-sulfinate hydrate

Produkt 1

HCID 54435877HCID 54435877, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24470Silver NitrateKatalysatorHCID 180AcetoneLösungsmittel2×
HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

A suspension of 4-nitrobenzyl 2-[(3R,4R)-4-[(benzothiazol-2-yl)dithio]-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methyl-3-butenoate (XIIIc, 3.25 g, 0.005 mole) in acetone (90 mL) and water (10 mL) was treated at room temperature with silver nitrate (1.06 g, 0.00625 mole), followed by treatment with a solution of sodium p-toluenesulfinate hydrate (0.90 g, 0.050 mole) in acetone (70 mL) - water (10 mL). The slurry was stirred for 1 h at room temperature under darkness. It was then filtered through Celite, which was washed with acetone. The volume of the filterate was reduced in vacuo, and the product was extracted into ether (3×250 mL). The ether phase was dried over magnesium sulfate and concentrated. Flash chromatography (silica gel, 50% ethyl acetate in hexane) gave the pure title product, XIIId, as a solid (2.053 g, 62%).

Aufarbeitung

  1. filtrationIt was then filtered through Celite, which
  2. washwas washed with acetone
  3. extractionthe product was extracted into ether (3×250 mL)
  4. dry with materialThe ether phase was dried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9aee73861e214a2dbb111ae1ed8ece4c
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05266691

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