反应 #54319

反应方程式

hydrochloric acid

tetrahydrofuran

benzhydryl 7-phenoxyacetamido-3-formyl-3-cephem-4-carboxylate-1-oxide

(1-methyl-1H-tetrazol-5-yl)methylenetriphenylphosphorane

→

benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate-1-oxide

收率 59.0%

溶剂

ethyl acetate

methanol

反应条件

后处理

1. 1
   温度after cooling to -5°--10° C.
2. 2
   洗涤The organic layer was washed with five portions of a saturated aqueous sodium chloride solution
3. 3
   干燥dried over anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
5. 5
   其他to leave a solid residue
6. 6
   workup.STIRRINGstirred at room temperature for 20 minutes
7. 7
   过滤filtered
8. 8
   其他leaving a precipitate

实验过程

To 130 ml of anhydrous tetrahydrofuran was added 5.35 g of benzhydryl 7-phenoxyacetamido-3-formyl-3-cephem-4-carboxylate-1-oxide, and, after cooling to -5°--10° C., further added 4.3 g of (1-methyl-1H-tetrazol-5-yl)methylenetriphenylphosphorane. The mixture was stirred at that temperature for 5 hours and poured into a mixture of ethyl acetate and ice-water. The resulting mixture was then made acidic with 10 ml of 5% hydrochloric acid. The organic layer was washed with five portions of a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to leave a solid residue. The residue was, after addition of approximately 30 ml of methanol, stirred at room temperature for 20 minutes and filtered leaving a precipitate. There was obtained 3.62 g of benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate-1-oxide as a crystalline powder. The filtrate was evaporated under redueced pressure to dryness, and the obtained residue was developed through silica gel column with ethyl acetate to give 600 mg of the crystals additionally.

来源