Pyridine → Benzhydryl 7-amino-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate
Reaction equation
N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C1(CC([NH:22][CH:23]2[C:50](=[O:51])[N:25]3[C:26]([C:34]([O:36][CH:37]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:35])=[C:27]([CH:30]=[C:31]([Br:33])[Br:32])[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.COCCO>C(Cl)Cl.O>[NH2:22][CH:23]1[C:50](=[O:51])[N:25]2[C:26]([C:34]([O:36][CH:37]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])=[C:27]([CH:30]=[C:31]([Br:33])[Br:32])[CH2:28][S:29][C@H:24]12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Pyridine (0.39 ml) was added to a suspension of phosphorus pentachloride (1.01 ml) in dry methylene chloride (25 ml) at 5° C., and the mixture was stirred at ambient temperature for 30 minutes. Benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate (2.5 g) was added to the above mixture at -10° C. and stirred for two-hours. Then, methylcellosolve (2.3 ml) was added to the reaction mixture at -30° C. and the resulting solution was stirred for an hour. To the above solution was added 5 ml of water and the separated organic layer was washed in turn with a saturated aqueous solution of sodium bicarbonate and brine, dried. The solvent was evaporated to give benzhydryl 7-amino-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate (1.7 g).
Workup
- stirringstirred for two-hours
- stirringthe resulting solution was stirred for an hour
- washthe separated organic layer was washed in turn with a saturated aqueous solution of sodium bicarbonate and brine
- customdried
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-1c0bf66e0455439ea5f32903983ce016
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04609730
Reaction notes
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