Pyridine → HCID 88683653, compound

HRID 1164428Notes

Reaction equation

HRID 1164428 reaction equation
[CH3:1][O:2][NH:3][C@@H:4]1[C:20](=[O:21])[N:6]2[C:7]([C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13])=[C:8]([CH3:11])[CH2:9][S:10][C@H:5]12.N1C=CC=CC=1.[O:28]([CH2:35][C:36](Cl)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl.C(OCC)(=O)C.O>[CH3:1][O:2][N:3]([CH:4]1[C:20](=[O:21])[N:6]2[C:7]([C:12]([O:14][CH2:15][C:16]([Cl:17])([Cl:18])[Cl:19])=[O:13])=[C:8]([CH3:11])[CH2:9][S:10][C@H:5]12)[C:36](=[O:37])[CH2:35][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 69703Phenoxyacetyl chlorideHCID 88684178HCID 88684178, compound

Product 1

HCID 88683653HCID 88683653, compoundYield 117.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-25 °C

Procedure

In methylene chloride (10 ml) are dissolved 2,2,2-trichloroethyl 7β-methoxyamino-3-methyl-3-cephem-4-carboxylate (320 mg) and pyridine (134 mg) and the mixture is cooled to -25° C. To this mixture is added phenoxyacetyl chloride (171 mg), followed by stirring for 20 minutes. The reaction mixture is poured in a mixture of ethyl acetate and water and the organic layer is taken. The organic layer is washed with 1 N-HCl, aqueous sodium hydrogen carbonate and aqeuous sodium chloride in that-order, dried over magnesium sulfate and concentrated. The above procedure gives 2,2,2-trichloroethyl 7-(N-methoxy-2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylate (510 mg).

Workup

  1. washThe organic layer is washed with 1 N-HCl, aqueous sodium hydrogen carbonate and aqeuous sodium chloride in that-order,
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eca04a93041140049f59a0760eb7c869
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

Loading…