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HCID 2835862, Verbindung → HCID 54184965, Verbindung

HRID 1283393
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1283393
[SH:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1.[CH3:8][C:9]1[CH2:16][S:15][CH:14]2[N:11]([C:12](=[O:27])[CH:13]2[NH:17][C:18](=[O:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]=1[C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29].[Cl-].[Ca+2].[Cl-]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:7][N:6]1[C:2]([S:1][S:15][CH:14]2[N:11]([CH:10]([C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:33])[Cl:34])=[O:29])[C:9]([CH3:16])=[CH2:8])[C:12](=[O:27])[CH:13]2[NH:17][C:18](=[O:26])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:3][N:4]=[N:5]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 2835862HCID 2835862, VerbindungHCID 5284359Calcium ChlorideHCID 178482017HCID 178482017, Verbindung

Produkt 1

HCID 54184965HCID 54184965, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6212
Chloroform
Lösungsmittel

Versuchsvorschrift

A solution of trichloroethyl 6β-phenylacetamido-penicillanate 1β-oxide (28.86 g) and 5-mercapto-1-methyl-tetrazole (6.96 g) in toluene (800 cc.) is heated under reflux for 3 hours, and the water formed during the reaction is removed as it is formed by passing the condensate over calcium chloride before reintroducing it into the reaction mixture. The solvent is evaporated under reduced pressure (12 mm Hg) at 40°C; the residue obtained is dissolved in chloroform (50 cc.) and the solution obtained is chromatographed on a column of silica (400 g) (0.06-0.20 mm, pH neutral; diameter of the column: 4.8 cm., height: 55 cm.). Elution is carried out using chloroform, collecting 250 cc. fractions. Fractions 10 to 17 are combined and concentrated to dryness under reduced pressure (12 mm Hg) at 40°C. 4-(1-Methyl-5-tetrazolyl-dithio)-3-phenylacetamido-1-(1-trichloroethoxycarbonyl-2-methyl-prop-2-en-1-yl)-2-azetidinone (17.4 g.) is obtained in the form of a colourless pastelike product, the characteristics of which are as follows: Rf = 0.50 [silica gel; chloroform/ethyl acetate (50/50 by volume)].

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. customis removed as it
  3. customis formed
  4. additionbefore reintroducing it into the reaction mixture
  5. customThe solvent is evaporated under reduced pressure (12 mm Hg) at 40°C
  6. customthe residue obtained
  7. customthe solution obtained
  8. customis chromatographed on a column of silica (400 g) (0.06-0.20 mm
  9. washElution
  10. customcollecting 250 cc
  11. concentrationconcentrated to dryness under reduced pressure (12 mm Hg) at 40°C

Quellen und Nachweise

ORD-Eintrag
ord-7beb014012684e7b87fbc9e775561fef
Quelldatensatz
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03975385

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