Reacción #56297

ord-5a172908a35746a1ae556a5be665f22e

Ecuación de reacción

CCOC(=O)NS(=O)(=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-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CCOC(=O)NS(=O)(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7β-amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid
Rendimiento 85.0%

Reactantes

CCOC(=O)NS(=O)(=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-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid
O=C(O)C(F)(F)F
trifluoroacetic acid

Reactivos

Ninguno

Disolventes

CCOCC
ether
—
acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroviscous residue is obtained
  2. 2
    OtroThe solid is triturated
  3. 3
    Filtracióncollected by filtration
  4. 4
    Lavadowashed with ether
  5. 5
    Secadodried over phosphorus pentoxide

Procedimiento

7β-(t-Butoxycarbonyl)amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (2.2 g) is dissolved in ice cooled solution of trifuoroacetic acid (20 ml) and the mixture is stirred for 20 minutes. Then trifluoroacetic acid is taken off under reduced pressure and viscous residue is obtained. The residue becomes solid upon addition of ether (50 ml). The solid is triturated, collected by filtration, washed with ether and dried over phosphorus pentoxide. The procedure provides 7β-amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (1.55 g).

Fuente

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