Reacción #56299

ord-6c56c5d8d468489080a200f90013b0c4

Ecuación de reacción

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
Rendimiento 86.7%

Reactantes

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

Reactivos

Ninguno

Disolventes

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

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooling
  2. 2
    ConcentraciónThe solution is concentrated and to the residue, ether (20 ml)
  3. 3
    workup.ADDITIONis added
  4. 4
    OtroThe resultant precipitate is triturated
  5. 5
    Filtracióncollected by filtration
  6. 6
    Lavadowashed with ether
  7. 7
    Secadodried over phosphorus pentoxide

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04224441uspto-grants-1980_09