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Acetic Acid → HCID 178482015, Verbindung

HRID 67698
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 67698
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.CN1C(C[N:26]2[C:30]([SH:31])=[N:29][N:28]=[N:27]2)=NN=N1.[C:32](O)(=O)[CH3:33].B(F)(F)F.CCOCC>O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH:5]([S:31][C:30]3[NH:29][N:28]=[N:27][N:26]=3)[CH2:33][C:32]3[N:26]([CH3:30])[N:27]=[N:28][N:29]=3)[CH2:15][S:14][C@H:9]12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178482016HCID 178482016, Verbindung

Produkt 1

HCID 178482015HCID 178482015, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

A solution of 1.54 g. of 7-aminocephalosporanic acid and 1.0 g. (5 mmole) of 1-(1-methyl-1H-tetrazol-5-ylmethyl)-1H-tetrazol-5-thiol in 7.0 ml. of glacial acetic acid was heated in an oil bath to a temperature of about 65°-70° C. To the hot reaction mixture were added 3.6 ml. of boron trifluoride etherate, and the reaction mixture was heated at a temperature of 65°-70° C. for one hour with stirring. The reaction mixture was then cooled to room temperature and 10 ml. of water were added. The reaction mixture was stirred for 15 minutes after water addition, was filtered, and then chilled in an ice bath. The pH of the cold mixture was adjusted to pH 4.5 with concentrated ammonium hydroxide. The precipitate which formed was filtered, washed repeatedly with water, with acetone, and finally with diethyl ether. The off-white solid product was vacuum dried for one hour at 40° C. There was obtained 1.5 g. (80% yield) of the title compound.

Aufarbeitung

  1. additionTo the hot reaction mixture were added 3.6 ml
  2. stirringThe reaction mixture was stirred for 15 minutes
  3. filtrationwas filtered
  4. temperaturechilled in an ice bath
  5. customThe precipitate which formed
  6. filtrationwas filtered
  7. washwashed repeatedly with water, with acetone
  8. customdried for one hour at 40° C
  9. customThere was obtained 1.5 g

Quellen und Nachweise

ORD-Eintrag
ord-c828cb921753496e9f48c31b62f15f2f
Quelldatensatz
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04346076

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