Dichloromethane → (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755865
[OH:1][NH:2][C:3]([C:5]1[N:15]=[C:8]2[N:9]=[C:10]([CH3:14])[CH:11]=[C:12]([SH:13])[N:7]2[N:6]=1)=[O:4].CC(O[CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=O.B(F)(F)F.CCOCC.ClCCl>S1(CCCC1)(=O)=O.ClCCl>[NH2:28][C@@H:25]1[C:26](=[O:27])[N:23]2[C@@H:24]1[S:29][CH2:30][C:21]([CH2:20][S:13][C:12]1[N:7]3[N:6]=[C:5]([C:3](=[O:4])[NH:2][OH:1])[N:15]=[C:8]3[N:9]=[C:10]([CH3:14])[CH:11]=1)=[C:22]2[C:31]([OH:33])=[O:32]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178429721HCID 178429721, Verbindung

Produkt 1

HCID 22855051(6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 69712587Dichloromethane sulpholaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-Hydroxy-7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidine-2-carboxamide and 3.4 g (12.5 mmol) of 7-aminocephalosporanic acid (3.1 g) (13.9 mmol) are suspended in 75 ml of sulpholane/dichloromethane (1:1 v/v). 7.5 ml of boron trifluoride etherate are added dropwise thereto at 0° C. and the mixture is stirred at 0° C. for 2.5 hours and at room temperature for 15 hours. 200 ml of dichloromethane are now added. After stirring for 30 minutes the mixture is suction filtered. The filter material is dissolved in 100 ml of water. The product is precipitated with saturated sodium hydrogen carbonate solution (pH~5), filtered off and washed with water, ethanol and ether. There are obtained 3.5 g of (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

Aufarbeitung

  1. stirringAfter stirring for 30 minutes the mixture
  2. filtrationfiltered
  3. dissolutionThe filter material is dissolved in 100 ml of water
  4. customThe product is precipitated with saturated sodium hydrogen carbonate solution (pH~5)
  5. filtrationfiltered off
  6. washwashed with water, ethanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-b3576f4a2abd4f508fb1e720816d09dc
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05438052

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