Reaktion #56299

ord-6c56c5d8d468489080a200f90013b0c4

Reaktionsgleichung

CCOC(=O)NC(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)OC(C)(C)C)[C@H]2SC1
7β-(t-Butoxycarbonyl)amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid
→
CCOC(=O)NC(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7β-amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid
Ausbeute 86.7%

Edukte

CCOC(=O)NC(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)OC(C)(C)C)[C@H]2SC1
7β-(t-Butoxycarbonyl)amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid

Reagenzien

Keine

Lösungsmittel

O=C(O)C(F)(F)F
trifluoroacetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooling
  2. 2
    EinengenThe solution is concentrated and to the residue, ether (20 ml)
  3. 3
    workup.ADDITIONis added
  4. 4
    SonstigeThe resultant precipitate is triturated
  5. 5
    Filtrationcollected by filtration
  6. 6
    Waschenwashed with ether
  7. 7
    Trocknendried over phosphorus pentoxide

Vorschrift

7β-(t-Butoxycarbonyl)amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (275 mg) is dissolved in trifluoroacetic acid (2 ml) under ice-cooling and the mixture is stirred for 20 minutes. The solution is concentrated and to the residue, ether (20 ml) is added. The resultant precipitate is triturated, collected by filtration, washed with ether and dried over phosphorus pentoxide. The procedure provides 7β-amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (195 mg). In NMR spectrum, this product is good agreement with the product obtained in Example 20.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04224441uspto-grants-1980_09