p-Toluenesulfonic acid → 2-[4-(Benzthiazol-2-yldithio)-2-oxo-3-phenoxyacetaminoazetidin-1-yl]-3-methyl-3-butenoic acid diphenylmethyl ester

HRID 279920

Reaktionsgleichung

Reaktionsgleichung von HRID 279920
[C:1]1(C)[CH:6]=CC(S(O)(=O)=O)=C[CH:2]=1.N([O:14][CH:15]([CH3:17])[CH3:16])=O.[C:18]1([CH:24]([O:31][C:32](=[O:53])[CH:33]([N:37]2[C:43](=[O:44])[CH:42]3[CH:38]2[S:39][C:40]([CH2:45]OC2C=CC=CC=2)=[N:41]3)[C:34]([CH3:36])=[CH2:35])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[SH:54][C:55]1[S:56][C:57]2[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=2[N:59]=1.C(OCC)(=[O:66])C>C(Cl)Cl>[C:25]1([CH:24]([O:31][C:32](=[O:53])[CH:33]([N:37]2[CH:38]([S:39][S:54][C:55]3[S:56][C:57]4[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=4[N:59]=3)[C:42]([NH:41][C:40]([CH3:45])=[O:66])([O:14][C:15]3[CH:17]=[CH:6][CH:1]=[CH:2][CH:16]=3)[C:43]2=[O:44])[C:34]([CH3:36])=[CH2:35])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

7

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 10929Isopropyl nitriteHCID 539374163-Methyl-2-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)-3-butenoic acid diphenylmethyl esterHCID 178418395HCID 178418395, Verbindung

Produkt 1

HCID 867407842-[4-(Benzthiazol-2-yldithio)-2-oxo-3-phenoxyacetaminoazetidin-1-yl]-3-methyl-3-butenoic acid diphenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

400 mg of 40% aqueous p-toluenesulphonic acid and 1.55 g (17 mmol) of isopropyl nitrite are added to a solution of 4.0 g (8 mmol) of 3-methyl-2-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)-3-butenoic acid diphenylmethyl ester in 12 ml of methylene chloride and the solution is stirred for 6 hours at room temperature with the exclusion of light. A solution of 1.67 g (10 mmol) of 2-mercaptobenzthiazole in 30 ml of ethyl acetate is then added dropwise in the course of 30 minutes and the whole is stirred for a further 12 hours at room temperature. After this period, the thin layer chromatogram indicates almost complete conversion to the title compound. Working up is carried out in a manner analogous to that described in Example 2 (a). The title compound has a melting point of 140°-141°.

Aufarbeitung

  1. stirringthe whole is stirred for a further 12 hours at room temperature
  2. waitAfter this period

Quellen und Nachweise

ORD-Eintrag
ord-991430fdca4643ad87d15af01b2a32af
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587048

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