Reacción #4357

ord-14d0b639897e4843a7bf6d6a18bfd472

Ecuación de reacción

CC(=O)CC(=O)OCC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1.[Na+]
sodium 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate
CC(C)CC(=O)OC(I)C(C)C
1-iodo-2-methylpropyl 3-methylbutyrate
→
CC(=O)CC(=O)OCC1=C(C(=O)OC(OC(=O)CC(C)C)C(C)C)N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1
title compound
Rendimiento 41.0%
CC(=O)CC(=O)OCC1=C(C(=O)OC(OC(=O)CC(C)C)C(C)C)N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1
1-(3-methylbutyryloxy)-2-methylpropyl 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate
Rendimiento 41.0%

Reactantes

CC(=O)CC(=O)OCC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1.[Na+]
sodium 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate
CC(C)CC(=O)OC(I)C(C)C
1-iodo-2-methylpropyl 3-methylbutyrate

Reactivos

Ninguno

Disolventes

CN(C)C=O
N,N-dimethylformamide

Condiciones de reacción

Temperatura
-5°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGby stirring for further 5 minutes

Procedimiento

In 30 ml of N,N-dimethylformamide is dissolved 4.76 g of sodium 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate and the solution is cooled to -5° C. With stirring, 5.0 g of 1-iodo-2-methylpropyl 3-methylbutyrate is added dropwise, followed by stirring for further 5 minutes. Thereafter, following the procedupe of Example 1, 2.5 g of the title compound is obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04725592uspto-grants-1988_02