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

HRID 1155152Notes

Reaction equation

HRID 1155152 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-287210e0fcc34112951b3144f62b29f2
Source dataset
uspto-grants-1981_11
Patent number
US04299829

Reaction notes

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