Pyridine → HCID 88601078, compound

HRID 1380975Notes

Reaction equation

HRID 1380975 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].N1C=CC=CC=1.C1(CC([NH:22][CH:23]2[C:50](=[O:51])[N:25]3[CH: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])=[CH:28][S:29][C@H:24]23)=O)C=CC=CC=1.C(OC(C)C)(C)C>ClCCl.O.CO>[ClH:2].[NH2:22][CH:23]1[C:50](=[O:51])[N:25]2[CH: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])=[CH:28][S:29][C@H:24]12

Participants

8

Reactant 4

HCID 1049PyridineHCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 88600993Benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-2-cephem-4-carboxylate

Product 1

HCID 88601078HCID 88601078, compoundYield 97.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of phosphorus pentachloride (13.74 g) in dichloromethane (150 ml) was dropwise added pyridine (5.34 ml) at -15° to -10° C. under stirring which was continued at the same temperature for 30 minutes. To the above mixture was added benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-2-cephem-4-carboxylate (29.4 g) at -5° C. After the reaction mixture was stirred at -5° for 1.5 hours, methanol (26.62 ml) was dropwise added to the reaction mixture under cooling at -20° and the mixture was stirred at -20° C. to -5° C. for 1.5 hours. Then water (30 ml) was added to the reaction mixture under ice-cooling. After the reaction mixture was stirred for an hour at the same temperature, diisopropylether (100 ml) was added to the reaction mixture at 0° C. The resultant precipitates were collected by filtration and washed in turn with water and diisopropyl ether to give benzhydryl 7-amino-3-(2,2-dibromovinyl)-2-cephem-4-carboxylate hydrochloride (25.23 g).

Workup

  1. customat -15° to -10° C.
  2. stirringAfter the reaction mixture was stirred at -5° for 1.5 hours
  3. temperatureunder cooling at -20°
  4. stirringthe mixture was stirred at -20° C. to -5° C. for 1.5 hours
  5. temperaturecooling
  6. additionwas added to the reaction mixture at 0° C
  7. customThe resultant precipitates
  8. filtrationwere collected by filtration
  9. washwashed in turn with water and diisopropyl ether

Sources & evidence

ORD record
ord-119eb050a3e44f3fabda8c17c74c0994
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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