Reacción #54381

ord-33ed86bd9a78465cbe69139ce8a64073

Ecuación de reacción

O=C(COc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(O)CS[C@H]12
7β-phenoxyacetamido-3-hydroxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester
C=[N+]=[N-]
diazomethane
COC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=O)COc3ccccc3)[C@H]2SC1
7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónthe solution is carefully concentrated
  2. 2
    Otrothe residue is dried under a high vacuum
  3. 3
    OtroThe residue is purified by thick layer chromatography (toluene/ethyl acetate, 3:1, silica gel)
  4. 4
    LavadoAfter eluting the silica gel of the zone at Rf = 0.17 with ethyl acetate
  5. 5
    Concentraciónconcentrating the solution
  6. 6
    Otroon a rotary evaporator

Procedimiento

The resulting crude 7β-phenoxyacetamido-3-hydroxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester is dissolved in methanol and a solution of diazomethane in ether is added at 0° C. After 10 minutes, the solution is carefully concentrated and the residue is dried under a high vacuum. The residue is purified by thick layer chromatography (toluene/ethyl acetate, 3:1, silica gel). After eluting the silica gel of the zone at Rf = 0.17 with ethyl acetate, and concentrating the solution on a rotary evaporator, 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester is obtained; melting point 120° C. (from ether).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04147864uspto-grants-1979_04