Boron trifluoride etherate → 7-Amino-3-(1,2,5-thiadiazol-3-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 34493

Reaktionsgleichung

Reaktionsgleichung von HRID 34493
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.[S:19]1[N:23]=[CH:22][C:21]([S-:24])=[N:20]1.[K+].B(F)(F)F.CCOCC>FC(F)(F)C(O)=O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:24][C:21]3[CH:22]=[N:23][S:19][N:20]=3)[CH2:15][S:14][C@H:9]12

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 23683003Potassium 1,2,5-thiadiazole-3-thiolate

Produkt 1

HCID 678873867-Amino-3-(1,2,5-thiadiazol-3-yl)thiomethyl-3-cephem-4-carboxylic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

7-Aminocephalosporanic acid (0.272 g) was added to the solution of potassium 1,2,5-thiadiazole-3-thiolate (0.136 g) in trifluoroacetic acid (5 ml) and the mixture was stirred for a few minutes until the solution turned clear, and then, boron trifluoride etherate (0.434 g) was added thereto and the mixture was stirred for 12 hours at room temperature. The reaction mixture was evaporated under reduced pressure and the residue was adjusted to pH 3.0 with 2% aqueous solution of ammonium hydroxide. The precipitates were collected by filtration, washed with cool water, acetone and diethyl ether and dried to give 7-amino-3-(1,2,5-thiadiazol-3-yl)thiomethyl-3-cephem-4-carboxylic acid (0.210 g).

Aufarbeitung

  1. stirringthe mixture was stirred for 12 hours at room temperature
  2. customThe reaction mixture was evaporated under reduced pressure
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with cool water, acetone and diethyl ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6c2d6420f00c4542bcf483518e402c71
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761410

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