反応 #54319

反応方程式

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

収率 59.0%

溶媒

ethyl acetate

methanol

反応条件

後処理

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

実験手順

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.

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