Reacción #214651

ord-59bb5088c0a448e5800af419cba94c5d

Ecuación de reacción

Cl
hydrochloric acid
[K+].[OH-]
potassium hydroxide
O
water
COC(=O)[C@H]1C(OC)=CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12
7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid methyl ester
→
COC1=CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C(=O)O
7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid

Reactantes

Cl
hydrochloric acid
[K+].[OH-]
potassium hydroxide
O
water
COC(=O)[C@H]1C(OC)=CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12
7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid methyl ester

Reactivos

Ninguno

Disolventes

ClCCl
methylene chloride
C1CCOC1
tetrahydrofurane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe methylene chloride phase is separated off
  2. 2
    Extracciónthe aqueous phase is extracted with 30 ml of methylene chloride
  3. 3
    SecadoThe combined organic phases are dried over sodium sulphate
  4. 4
    Concentraciónconcentrated by evaporation in vacuo
  5. 5
    OtroThe residue is crystallised from chloroform/diethyl ether

Procedimiento

15 ml of cooled 0.1 N aqueous potassium hydroxide solution are added, whilst stirring, to a solution, cooled in an ice bath, of 382 mg of 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid methyl ester in 30 ml of tetrahydrofurane. After 5 minutes, 100 ml of water and 70 ml of methylene chloride are added and the mixture is acidified by adding 10 ml of 1 N aqueous hydrochloric acid. The methylene chloride phase is separated off and the aqueous phase is extracted with 30 ml of methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is crystallised from chloroform/diethyl ether and gives 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid of melting point 142° C. (decomposition).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04255328uspto-grants-1981_03