Reacción #54865

ord-2597a13f2a1849b4a8a94d6abd6618e3

Ecuación de reacción

O=C([O-])O.[Na+]
NaHCO3
O=C(Cl)Cc1ccco1
2-furylacetyl chloride
Cn1nnnc1SCC1=C(P(=O)([O-])[O-])N2C(=O)[C@@H](N)[C@H]2SC1
7β-amino-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate
Cl
HCl
→
Cn1nnnc1SCC1=C(P(=O)([O-])[O-])N2C(=O)[C@@H](NC(=O)Cc3ccco3)[C@H]2SC1.[Na+].[Na+]
title compound
Cn1nnnc1SCC1=C(P(=O)([O-])[O-])N2C(=O)[C@@H](NC(=O)Cc3ccco3)[C@H]2SC1.[Na+].[Na+]
Disodium 7β-(2-furylacetamido)-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate

Reactantes

O=C([O-])O.[Na+]
NaHCO3
O=C(Cl)Cc1ccco1
2-furylacetyl chloride
Cn1nnnc1SCC1=C(P(=O)([O-])[O-])N2C(=O)[C@@H](N)[C@H]2SC1
7β-amino-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate
Cl
HCl

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone
O
water
CC(C)=O
acetone
CC(C)=O
acetone
O
water
CCOC(C)=O
EtOAc

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONthe aqueous solution added to 100 ml
  2. 2
    Otrothe ethyl acetate layer separated
  3. 3
    Otroevaporated

Procedimiento

To a solution of 10 mmoles 7β-amino-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate in 100 ml. water and 100 ml. acetone containing 5 g. NaHCO3 is added 20 mmoles 2-furylacetyl chloride in 40 ml acetone at 0° C. After 1 hr. stirring at 0° and 2 hrs at 25° the acetone is pumped off in vacuo and the aqueous solution added to 100 ml. water and 200 ml. EtOAc. The pH is adjusted to 2 with HCl and the ethyl acetate layer separated, and evaporated. The residue is taken up in 50 ml water containing 1.6 g. NaHCO3 and lyophilized, providing the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04150223uspto-grants-1979_04