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Hydrochloric Acid → p-Nitrobenzyl 3-hyroxy-7-phenoxyacetamido-3-cephem-4-carboxylate

HRID 325476
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 325476
C1(CO[C:6]([S:8][CH:9]2[N:12]([C:13](=C(N3CCOCC3)CBr)[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C:11](=[O:36])[CH:10]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)CC1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:52][OH:53].Cl>C(Cl)Cl>[OH:53][C:52]1[CH2:6][S:8][C@@H:9]2[CH:10]([NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:11](=[O:36])[N:12]2[C:13]=1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6451240Aluminum(III) ChlorideHCID 53903289HCID 53903289, Verbindung

Produkt 1

HCID 67616247p-Nitrobenzyl 3-hyroxy-7-phenoxyacetamido-3-cephem-4-carboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-[2-bromo-1-(morpholin-4-yl)ethylidene]acetate (151 mg) in methylene chloride (1.5 ml) is added aluminum chloride (0.42 mg) and the mixture is stirred for 50 minutes under ice cooling. The mixture is diluted with ice water (2 ml), stirred for 5 minutes, and stirred with a mixture (15 ml) of methanol and methylene chloride (5:1) after addition of 10% hydrochloric acid (3 ml) at room temperature for 80 minutes. The reaction mixture is diluted with ice water, and is extracted with chloroform. The extract solution is washed with water, dried over magnesium sulfate, and evaporated to give p-nitrobenzyl 3-hydroxy-7-phenoxyacetamido-3-cephem-4-carboxylate (63 mg). Yield: 63%. This product is identical with the product of Example 4.-III(3) produced by hydrolysis of the 4-morpholino group to be replaced with the corresponding hydroxy group.

Aufarbeitung

  1. stirringstirred for 5 minutes
  2. extractionis extracted with chloroform
  3. washThe extract solution is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-58265f666ffa41538e682ffe99e08631
Quelldatensatz
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04440683

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