Diazomethane → 2,2,2-Trichloroethyl 2-methyl-7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

HRID 28280Notes

Reaction equation

HRID 28280 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:5]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[C:20](=[N:25][OH:26])[C:21](=[O:24])[CH2:22][Br:23])[C@H:4]2[S:3]1.[N+](=[CH2:31])=[N-]>C(O)C.C(OCC)C>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][C:12]([Cl:13])([Cl:14])[Cl:15])=[O:9])[N:5]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[C:20](=[N:25][O:26][CH3:31])[C:21](=[O:24])[CH2:22][Br:23])[C@H:4]2[S:3]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 178427241HCID 178427241, compound

Product 1

HCID 1317114922,2,2-Trichloroethyl 2-methyl-7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-hydroxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (a mixture of syn and anti isomers) (1.2 g.) in ethanol (20 ml.) was added dropwise a solution of diazomethane (0.1 mole) in diethyl ether under stirring and ice-cooling to complete the reaction. After the reaction mixture was concentrated under reduced pressure, the residue was pulverized in diisopropyl ether, collected by filtration and then dried to give brown powder of 2,2,2-trichloroethyl 2-methyl-7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (a mixture of syn and anti isomers) (1.1 g.), mp 80° to 83° C. (dec.).

Workup

  1. temperatureice-cooling
  2. customthe reaction
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-deb608813f7a4757b815911ca58ff0a7
Source dataset
uspto-grants-1980_09
Patent number
US04225707

Reaction notes

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