Reaktion #550585

ord-3376e4de16e04911808a2ffa82acbb0f

Reaktionsgleichung

CCOC(C)=O
Ethyl acetate
[Al+3].[Cl-].[Cl-].[Cl-]
Aluminum chloride
CON=C(C(C)=O)C(=O)NC1C(=O)N2C(C(=O)O)=CCS[C@H]12
7-(2-methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid
Br.c1cc[nH+]cc1
Pridinium hydrobromide
CON=C(C(=O)CBr)C(=O)NC1C(=O)N2C(C(=O)O)=CCS[C@H]12
7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONthe mixture was treated in a similar manner to that of the above Example 10-(8)

Vorschrift

Aluminum chloride (120 mg.) was added to a solution of 7-(2-methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 50 mg.) in dry tetrahydrofuran (10 ml.). Pridinium hydrobromide perbromide (50 mg.) was added to the solution, and stirred at room temperature for 20 minutes. Ethyl acetate (50 ml.) and water (10 ml.) were added to the resultant solution and the mixture was treated in a similar manner to that of the above Example 10-(8) to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 52.5 mg.)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04518774uspto-grants-1985_05