Reaktion #96130

Reaktionsgleichung

diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(2-chloro-1-hydroxyethylidene)acetate

methanol

hydrochloric acid

→

diphenylmethyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionis extracted with methylene chloride
2. 2
   WaschenThe extract solution is washed with 5% aqueous sodium hydrogen carbonate solution and water
3. 3
   Trocknendried over sodium sulfate
4. 4
   Sonstigeevaporated
5. 5
   SonstigePurification of the obtained residue by thin-layer chromatography
6. 6
   workup.ADDITIONa mixture of benzene and ethyl acetate (3:2)

Vorschrift

To an ice cooled solution of diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(2-chloro-1-hydroxyethylidene)acetate (36 mg) in a mixture of methanol and tetrahydrofuran (1:1) (1.1 ml) is added 1 N-hydrochloric acid (0.39 ml), warmed to the room temperature, and the mixture is stirred for 1.5 hours. The reaction mixture is poured into ice water, and is extracted with methylene chloride. The extract solution is washed with 5% aqueous sodium hydrogen carbonate solution and water, dried over sodium sulfate, and evaporated. Purification of the obtained residue by thin-layer chromatography using a mixture of benzene and ethyl acetate (3:2) gives diphenylmethyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate (6 mg). m.p. 125°-126° C.

Quelle