Water → HCID 15384987, compound

HRID 744865Notes

Reaction equation

HRID 744865 reaction equation
[CH:1]([NH:3][CH:4]1[C:38](=[O:39])[N:6]2[C:7]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:8]([CH2:12][O:13][C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH2:9][S:10](=O)[C@H:5]12)=[O:2].C(OCC)(=O)C.O>CN(C)C=O.P(Cl)(Cl)Cl>[CH:1]([NH:3][CH:4]1[C:38](=[O:39])[N:6]2[C:7]([C:22]([O:24][CH:25]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:8]([CH2:12][O:13][C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 15384988HCID 15384988, compound

Product 1

HCID 15384987HCID 15384987, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24387Phosphorus trichlorideSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of benzhydryl 7-formamido-3-(1-piperidinyl)carbonyloxymethyl-3-cephem-4-carboxylate-1-oxide (2.07 g) in N,N-dimethylformamide (25 ml), phosphorus trichloride (1 ml) was added under cooling in a dry ice-ethanol bath (-60° C.), followed by stirring for 35 minutes. The reaction mixture was successively added with ethyl acetate and water under cooling in a dry ice-ethanol bath and then, the resulting mixture was increased to room temperature. The ethyl acetate layer was collected and the water layer was extracted further with ethyl acetate. Both ethyl acetate layers were combined together, successively washed with water and a saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby benzhydryl 7-formamido-3-(1-piperidinyl)carbonyloxymethyl-3-cephem-4-carboxylate (1.87 g, 93.0%) was obtained.

Workup

  1. temperatureunder cooling in a dry ice-ethanol bath
  2. temperaturethe resulting mixture was increased to room temperature
  3. customThe ethyl acetate layer was collected
  4. extractionthe water layer was extracted further with ethyl acetate
  5. washsuccessively washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and then dried over magnesium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-ebb1661295784506b27ef6540829981a
Source dataset
uspto-grants-1996_09
Patent number
US05559225

Reaction notes

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