Reaktion #1991828

Reaktionsgleichung

Benzhydryl 7-(phenoxyacetamido)-3-(triphenylphosphoran-diylmethyl)-3-cephem-4-carboxylate

4-methylthiazol-5-carboaldehyde

→

7-(phenoxyacetamido)-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid benzhydryl ester

Ausbeute 59.4%

Lösungsmittel

methylene chloride

sodium bicarbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at ambient temperature
2. 2
   Sonstigeseparated into the aqueous phase and organic solvent phase
3. 3
   SonstigeThe aqueous phase was removed
4. 4
   Waschenwashed with methylene chloride (20 ml)
5. 5
   Sonstigeseparated
6. 6
   TrocknenThe combined solution was dried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated to dryness under reduced pressure
8. 8
   SonstigeThe solid residue obtained
9. 9
   Sonstigewas purified chromatographically on a column of silica gel (Wako gel C-300) (40 g)

Vorschrift

Benzhydryl 7-(phenoxyacetamido)-3-(triphenylphosphoran-diylmethyl)-3-cephem-4-carboxylate (1.55 g ) and 4-methylthiazol-5-carboaldehyde (0.305 g) were dissolved in methylene chloride (20 ml), to which aqueous saturated sodium bicarbonate (20 ml) was added at ambient temperature. The resultant mixture was stirred for 17 hours at ambient temperature. The mixture was allowed to stand until it separated into the aqueous phase and organic solvent phase. The aqueous phase was removed and washed with methylene chloride (20 ml), and the washings (in methylene chloride) were combined with the organic solvent phase separated. The combined solution was dried over anhydrous magnesium sulfate and then concentrated to dryness under reduced pressure. The solid residue obtained was purified chromatographically on a column of silica gel (Wako gel C-300) (40 g) as developed with benzene-ethyl acetate (5:1) as the development solvent. The entitled compound, 7-(phenoxyacetamido)-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid benzhydryl ester (0.741 g) was obtained.

Quelle