반응 #54319

반응 방정식

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

수율 59.0%

용매

ethyl acetate

methanol

반응 조건

후처리

1. 1
   온도after cooling to -5°--10° C.
2. 2
   세척The organic layer was washed with five portions of a saturated aqueous sodium chloride solution
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
5. 5
   기타to leave a solid residue
6. 6
   workup.STIRRINGstirred at room temperature for 20 minutes
7. 7
   여과filtered
8. 8
   기타leaving a precipitate

실험 절차

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.

출처