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Methanol → 3-Formyl-7betaphenylacetylamino-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

HRID 1462053
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1462053
[CH:1]([C:3]1[C@H:8]([C:9]([OH:11])=[O:10])[N:7]2[C:12](=[O:24])[C@@H:13]([NH:14][C:15](=[O:23])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:6]2[S:5][CH:4]=1)=[O:2].O1CCOCC1.CO.[C:33]1([C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[N+]=[N-])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1CCCCC1>[C:33]1([CH:39]([O:10][C:9]([C@@H:8]2[N:7]3[C:12](=[O:24])[C@@H:13]([NH:14][C:15](=[O:23])[CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C@H:6]3[S:5][CH:4]=[C:3]2[CH:1]=[O:2])=[O:11])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 312751,4-DioxaneHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 887161643-Formyl-7beta-phenylacetylamino-ceph-2-em-4alpha-carboxylic acid

Produkt 1

HCID 113527753-Formyl-7betaphenylacetylamino-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

A solution of 10 g of 3-formyl-7β-phenylacetylamino-ceph-2-em-4α-carboxylic acid in 250 ml of a 4:1 mixture of dioxane and methanol is treated with a solution of 1.5 mol equivalents of diphenyldiazomethane in cyclohexane. After 2 hours at room temperature, the red-violet solution is evaporated to dryness under reduced pressure. The residue is dissolved in hot methylene chloride; the solution is diluted with cyclohexane whilst warm, and 3-formyl-7β-phenylacetylamino-ceph-2-em-4α-carboxlic acid diphenylmethyl ester is obtained in practically quantitative yield in the form of fine colourless felted needles, melting point 175.5°-176° C. (uncorrected, decomposition); [α]D20 =+513°±1° (c=1,084 in chloroform); thin layer chromatogram (silica gel): Rf=0.35 (system: toluene/acetone, 80:20) and Rf=0.58 (system: toluene/acetone 65:35); ultraviolet absorption spectrum (in 95% ethanol): λmax =289 mμ (ε=20,200) and λmin =245 mμ (ε= 2,100); infrared absorption spectrum: characteristic bands at 2.92μ, 3.53μ, 5.59μ, 5.72μ, 5.91μ, 6.34μ, 6.61μ and 6.67μ (in methylene chloride) and at 3.00μ, 5.63μ, 5.76μ, 5.95μ (double band), 5.99μ, 6.07μ and 6.58μ (in mineral oil).

Aufarbeitung

  1. customthe red-violet solution is evaporated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in hot methylene chloride
  3. additionthe solution is diluted with cyclohexane
  4. temperaturewhilst warm

Quellen und Nachweise

ORD-Eintrag
ord-98a1ffdf7c644b3fa02a1795845764e8
Quelldatensatz
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04458069

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