Phosphorus pentachloride → HCID 88645023, compound

HRID 1262754Notes

Reaction equation

HRID 1262754 reaction equation
[P].P(Cl)(Cl)(Cl)(Cl)Cl.C1(CC([NH:17][CH:18]2[C:52](=[O:53])[N:20]3[C:21]([C:36]([O:38][CH:39]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[O:37])=[C:22]([O:25][S:26]([C:29]4[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=4)(=[O:28])=[O:27])[CH2:23][S:24][C@H:19]23)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO.N1C=CC=CC=1>[NH2:17][CH:18]1[C:52](=[O:53])[N:20]2[C:21]([C:36]([O:38][CH:39]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[O:37])=[C:22]([O:25][S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH2:23][S:24][C@H:19]12

Participants

8

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 5462309PhosphorusHCID 12098361HCID 12098361, compound

Product 1

HCID 88645023HCID 88645023, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of phosphorus pentachloridepyridine complex prepared from phosphorus pentachloride (2.05 g) and pyridine (0.8 ml) in methylene chloride (40 ml) was added benzhydryl 7-phenylacetamido-3-tosyloxy-3-cephem-4-carboxylate (4.3 g) under ice-cooling with stirring. The mixture was stirred at the same temperature for 30 minutes and cooled in a dry ice-acetone bath. To the solution was added methanol (6 ml) at -30° C. and the mixed solution was stirred at -10° to -5° C. for an hour. The resulting solution was adjusted to pH 6.5 with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (100 ml). The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give benzhydryl 7-amino-3-tosyloxy-3-cephem-4-carboxylate (3.1 g)

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. temperaturecooled in a dry ice-acetone bath
  4. stirringthe mixed solution was stirred at -10° to -5° C. for an hour
  5. extractionextracted with ethyl acetate (100 ml)
  6. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3bc99a9bca9e4037a65f258d4171d02c
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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